Month: April 2022

HPLC of Formula: 1265884-98-7. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls. Author is Zhang, Mao-Mao; Wang, Ya-Ni; Wang, Bao-Cheng; Chen, Xiao-Wang; Lu, Liang-Qiu; Xiao, Wen-Jing.

Catalytic asym. cycloadditions via transition-metal-containing dipolar intermediates are a powerful tool for synthesizing chiral heterocycles. However, within the field of palladium catalysis, compared with the well-developed normal electron-demand cycloadditions with electrophilic dipolarophiles, a general strategy for inverse electron-demand ones with nucleophilic dipolarophiles remains elusive, due to the inherent linear selectivity in the key palladium-catalyzed intermol. allylations. Herein, based on the switched regioselectivity of iridium-catalyzed allylations, two asym. [4+2] cycloadditions of vinyl aminoalcs. with aldehydes and β,γ-unsaturated ketones through synergetic iridium and amine catalysis were achieved. The activation of vinyl aminoalcs. by iridium catalysts and carbonyls by amine catalysts provide a foundation for the subsequent asym. [4+2] cycloadditions of the resulting iridium-containing 1,4-dipoles and (di)enamine dipolarophiles. The former provides a straightforward route to a diverse set of enantio-enriched hydroquinolines bearing chiral quaternary stereocenters, and the later represent an enantio- and diastereodivergent synthesis of chiral hydroquinolines.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides.Related Products of 1265884-98-7.

Iridium-catalyzed enantioselective allylic alkylation of branched racemic carbonates R1CH(OBoc)CH:CH2 (R1 = MeCH:CH, Ph, 3-MeOC6H4, 3-thienyl, 2-naphthyl, PhCH2CH2CC, etc.) with functionalized alkylzinc bromide reagents R2ZnBr [R2 = EtO2C(CH2)3, NC(CH2)4, 1,3-dioxolan-2-ylmethyl, etc.] is described. Enabled by a chiral Ir/(P,olefin) complex, this method allows allylic substitution with various primary and secondary alkyl nucleophiles with excellent regio- and enantioselectivities. The developed reaction was showcased in a concise, asym. synthesis of (-)-preclamol.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Electric Literature of C12H15ClN2O2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about I+/TBHP Catalysis For Tandem Oxidative Cyclization To Indolo[2,3-b]quinolines. Author is Uyanik, Muhammet; Tanaka, Hiroki; Ishihara, Kazuaki.

A chemoselective tandem oxidative cyclization/aromatization of indole derivatives tethered to aniline sulfonamides using catalytic amount of tetrabutylammonium in the presence of tert-Bu hydroperoxide (TBHP) as an oxidant under nearly neutral conditions at room temperature is reported. The corresponding indolo[2,3-b]quinolines were obtained as sulfonate salts, which could be easily isolated in anal. pure form via only a simple filtration of the crude reaction mixture The natural product quinindoline could be easily obtained after basic work-up of the sulfonate salt. Control experiments revealed that both ionic and radical active species could be generated in situ under mild conditions for the corresponding oxidative transformations to proceed in a chemoselective manner.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Biosynthesis of penicillins. VI. N-2-Hydroxyethyl amides of some polycyclic and heterocyclic acetic acids as precursors》. Authors are Jones, Reuben G.; Soper, Quentin F.; Behrens, Otto K.; Corse, Joseph W..The article about the compound:2-Bromo-6-(bromomethyl)naphthalenecas:305798-02-1,SMILESS:BrCC1=CC2=CC=C(Br)C=C2C=C1).Name: 2-Bromo-6-(bromomethyl)naphthalene. Through the article, more information about this compound (cas:305798-02-1) is conveyed.

2,6-MeC10H6NH2 (78 g.) in 80 mL. concentrated HCl and 200 mL. H2O at 0°, treated at 5° with 35 g. NaNO2 in 50 mL. H2O and, after 0.5 h., with 130 g. ice-cold 42% HBF4, gives 90% of the 2-diazonium fluoroborate, decomposition of which yields 69% 2-methyl-6-fluoronaphthalene (I), m. 77°. I (40 g.) at 210°, treated (15 min.) with 40 g. Br (with illumination with a 100-w. lamp), gives 82% 2-(bromomethyl)-6-fluoronaphthalene (II), b2 125-30°, m. 53°. II (48 g.), added to a refluxing solution of 30 g. KCN in 60 mL. H2O and 200 mL. EtOH, the EtOH removed after refluxing 4 h., 500 mL. H2O added, the solution extracted with ether, and the residue from the ether boiled 5 h. with 40 g. KOH in 40 mL. H2O and 200 mL. EtOH, gives 74% 6-fluoro-2-naphthaleneacetic acid, m. 138-9° (Me ester, b2 163-6°, m. 48-9°). 2,6-MeC10H6NH2 (63 g.) in 100 mL. H2O and 700 g. 48% HBr, treated (3-4 h.) at 5° with 45 g. NaNO2 in 75 mL. H2O and the diazonium solution poured (10 min.) into 170 g. CuBr in 800 mL. 48% HBr at 70-80°, gives 40% 6-bromo-2-methylnaphthalene (III), m. 142° III yields 80% 6-bromo-2-(bromomethyl)naphthalene, m. 124-5° this gives 69% 6-bromo-2-naphthaleneacetic acid, m. 175-6° (Me ester, b2 187-93°, m. 67-9°). 3,2-ClC10H6CHO (32.5 g.), 35 g. hippuric acid, 14.5 g. anhydrous AcONa, and 50 mL. Ac2O, heated on the steam bath 1 h., give 75% 2-phenyl-4-(3-chloro-2-naphthylmethylene)-5(4H)-oxazolone (IV), bright yellow, m. 192° 40 g. IV in 200 mL. 10% NaOH, refluxed 9 h., the mixture diluted to 1500 mL. with H2O, washed with ether, the aqueous solution treated with 20 mL. 12.5 N NaOH and 15 mL. 30% H2O2, allowed to stand overnight, the filtrate acidified with HCl, extracted with ether-C6H6, and the residue esterified, gives 37% Me 3-chloro-2-naphthaleneacetate, b2 163-5°, m. 49-50° the free acid m. 193-4°. 6,2-MeOC10H6Ac (100 g.), 25.5 g. S, and 87 g. morpholine, heated 18 h. at 140°, part of the morpholine removed in vacuo, 250 mL. AcOH and 350 mL. concentrated HCl added, and the mixture refluxed 24 h., give 67% 6-methoxy-2-naphthaleneacetic acid, m. 203-5° (Me ester, b1 192-3°, m. 86°, 73%). 5,6,7,8-Tetrahydro-2-acetonaphthone (50 g.), 13 g. S, and 40 mL. morpholine, refluxed overnight, 400 mL. concentrated HCl and 300 mL. H2O added, and the mixture again refluxed overnight, followed by esterification with EtOH and H2SO4, give Et 5,6,7,8-tetrahydro-2-naphthaleneacetate, b0.5 140-3°. 2-Acetylphenanthrene (13.2 g.), 3.2 g. S, and 10.5 g. morpholine, heated 15 h. at 160°, the mixture treated with 150 mL. AcOH and 36% HCl, and refluxed 24 h., give 81% 2-phenanthreneacetic acid, m. 187-8° the 3-isomer m. 174-5°, 84% (Me ester, b1.5 203-5°, 89%). 8-(Bromomethyl)quinoline (120 g.) in 250 mL. warm EtOH, added (0.5 h.) to 50 g. KCN in 100 mL. warm H2O and the mixture refluxed 1.5 h., gives 78% 8-(cyanomethyl)quinoline, m. 86-7°; hydrolysis with aqueous alc. KOH and esterification give 91% Et 8-quinolineacetate, b3 158-60°. Et 3-quinolinecarboxylate (70 g.), 62 g. AcOEt, and EtONa (12 g. Na and 0.52 mol absolute EtOH) in 100 cc. dry C6H6, refluxed 20 h., the cooled solution poured onto ice, diluted to 5 l. with H2O, treated with 50 mL. 12 N NaOH, washed with two 300 mL. portions of ether, and the aqueous solution neutralized with dilute H2SO4 and extracted with two 500-mL. portions of ether, give 75% Et 3-quinolylformylacetate, m. 84° 27 g. of the keto ester in 125 g. 25% H2SO4, heated 30 min. at 100°, gives 95% 3-acetylquinoline (V). V (7 g.), 5 g. S, 50 mL. (NH4)2S, and 25 mL. H2O, heated 20 h. at 145-50°, the residue extracted with two 300-mL. portions boiling 5% HCl, the solution refluxed 3 h., and the crude acid esterified, give 19% Et 3-quinolineacetate, b2.5 140-2°. pH2NC6H4CH2CO2H (46 g.), 10.5 g. FeSO4, 115 g. C3H5(OH)3, 23 g. PhNO2, and 53 mL. concentrated H2SO4, boiled 5 h., give 37 g. crude acid which, esterified with EtOH and HCl, gives 39% Et 6-quinolineacetate, b3 160° the free acid (VI) m. 218-20°. Et 6-quinolinecarboxylate and AcOEt, condensed with EtONa, give 87% Et 6-quinolineacetate, hydrolysis of which with 25% H2SO4 at 100° gives 90% 6-acetylquinoline, m. 76° the Willgerodt reaction gives 87.5% VI. 3,4 O2N(H2N)C6H3CO2H (108 g.) in 350 mL. concentrated HCl, treated with 125 g. Sn in portions (temperature below 90°), gives 87% (3,4-diaminophenyl)acetic acid-2HCl (VII), m. 222-4° (decomposition); Et ester-2HCl (VIII), m. 185-7° (decomposition); 3 g. VII and 20 mL. 98-100% HCO2H, heated several hrs., give 100% 5-benzimidazoleacetic acid-HCl, m. 240-2° the Et ester m. 65-6°, 75%. VIII (14 g.) in 200 mL. ice H2O, treated with excess COCl2, gives 95% Et 2-hydroxy-5-benzimidazoleacetate, m. 208-9°. NCCH2CO2Et (113 g.) and 15 g. (HOCH2CH2)3N in 100 mL. absolute EtOH, treated with a slow stream of H2S, the mixture poured after 5 days into ice-H2O, and 38 g. of the resulting oil and 23.1 g. ClCH2Ac in 300 cc. anhydrous ether kept 4 days, give 20.6 g. Et 4-methyl-2-thiazoleacetate, b17 136-9°. Thiaxanthydrol (42 g.), 30 g. CH2(CO2H)2, and 80 mL. C5H5N, heated 2 h. at 60-70° and 2 h. at 90-5° and the liquid poured into 600 mL. 2 N HCl, give 90% 9-thiaxantheneacetic acid, m. 167-8° (Me ester, b2 182-4°). The Ag salt of 2-benzylimidazole (53 g.) and 50 g. BrCH2CO2Et in 200 mL. xylene, refluxed 48 h., give 25.4% of the Et ester, m. 70-70.5°, of 2-benzyl-1-imidazoleacetic acid, m. 173-4°. Me 1-acenaphtheneacetate, b4 176-8°. N-2-Thienylacetyl-DL-valine m. 110-12°. Amides were prepared by heating the Me or Et ester of the various acids with a slight excess of HOCH2CH2NH2 at 100-150° for several hrs.; R in RCH2CONHCH2CH2OH is given, together with S (see part V). 2-C10H7 m. 125-7°, S 1.3; 1-bromo-2-naphthalene m. 155-6°, S 0.5; 6-fluoro-2-naphthalene m. 145-6°, S 1.2; 3-chloro-2-naphthalene m. 150-1°, S 0.3; 6-bromo-2-naphthalene m. 167-8°, S 0.9; 5,6,7,8-tetrahydro-2-naphthalene m. 88-90°, S 0.9; 1-nitro-2-naphthalene m. 154-5°, S 0.9; 6-methoxy-2-naphthalene m. 160°, S 1.1; 1-acenaphthene m. 160°, S 1.1; 9-fluorene m. 127-8°, S 0.7; 2-phenanthrene m. 135-7°, S 0.5; 3-isomer m. 133-5°, S 0.5; 1-pyrrole m. 85-7°, S 0.9; 2-thiophene m. 66-7°, S 1.8; 2-furan oil, S 0.4; 2,6-dihydroxy-5-pyrimidine m. 271-2°, S 1; 2-methyl-4-hydroxy-5-pyrimidine m. 184°, S 0.9; 3,4-methylenedioxyphenyl m. 99-100°, S 1; 2-methyl-4-thiazole m. 93-4°, S 0.85; 4-methyl-2-thiazole m. 80-2°, S 0.9; 2-pyridine m. 93-4°, S 1; 3-isomer m. 94° S 1; 6-methyl-2-pyridine m. 49-50°, S 1; 2-benzyl-1-imidazole m. 177-9°, S 1; 3-quinoline m. 151-2°, S 1; 6-isomer m. 135°, S 1; 8-isomer m. 92-3°, S 1; 2-benzimidazole m. 185-90°, S 1; 5-isomer m. 160-2°, S 1; 2-hydroxy-5-benzimidazole m. 245-6°, S 1; 7-hydroxy-4-coumarin m. 114-16°, S 1; 9-xanthene m. 157-8°, S 0.8; 9-thiaxanthene m. 148-9°, S 0.7; 5-hydantoin m. 160-2°, S 0.9. Only a few of these compounds appeared to be utilized readily by the mold for the formation of new penicillins. Several of the compounds appeared to effect some increase in penicillin yield or to change the differential assay value of the crude penicillin produced in their presence.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Application of 1265884-98-7. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations. Author is Petrone, David A.; Isomura, Mayuko; Franzoni, Ivan; Rossler, Simon L.; Carreira, Erick M..

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution products (93-99% ee) with complete regiocontrol (>50:1 rr in all cases) over the undesired 1,3-dienes isomers which are obtained predominantly in the case of other metal catalysts. The synthetic utility of the products obtained was highlighted in a variety of stereoselective transition metal-catalyzed difunctionalization reactions. Furthermore, a combination of computational and exptl. studies supports a putative reaction mechanism wherein enantiodetermining C-C coupling occurs via nucleophilic attack on a highly planarized aryl butadienyl π-system that is coordinated to the Ir center in an η2-fashion.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Name: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Kinetic Resolution of Spiroindolines through Ir-Catalyzed Asymmetric Allylative Ring-Opening Reaction. Author is Qiao, Jianhui; Chang, Wenju; Zhao, Wenxuan; Liang, Yong; Wang, Shaozhong.

Kinetic resolution of racemic spiroindolines I [R = H, Me, MeO, F, Cl; X = H, Me, Cl; Y = H, Me, MeO, F, Cl; Z = H, Me, MeO, F; no stereo] with s factors of ≤15200 was developed to access enantiomerically enriched indole-annulated medium-sized lactams II [R1 = Ph, 2-thienyl, 2-naphthyl, etc.] and spiroindolines I [stereo = R] through Ir-catalyzed asym. allylative ring-opening reaction. D. functional theory calculations supported the idea that the accurate discrimination of two spiroindoline enantiomers by (η3-allyl)-iridium(III) species and the perfect central-to-axial chirality conversion during C-C bond fragmentation ensure the stereoselective formation of two contiguous stereogenic centers and one axis in the medium-sized lactams.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 4360-63-8, is researched, Molecular C4H7BrO2, about Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions, the main research direction is bicyclic aza arene preparation; tricyclic aza arene preparation; enolizable carbonyl compound aza arene annulation scandium triflate catalyst.Name: 2-Bromomethyl-1,3-dioxolane.

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called N-Cyanation of Primary and Secondary Amines with Cyanobenziodoxolone (CBX) Reagent, published in 2021-10-25, which mentions a compound: 7524-52-9, mainly applied to cyanamide preparation; amine cyanobenziodoxolone electrophilic cyanation; N-cyanation; amines; cyanamides; cyanobenziodoxolone; electrophilic cyanation, SDS of cas: 7524-52-9.

An efficient electrophilic N-cyanation of amines e.g., pyrrolidine with a stable and less-toxic 1-cyano-1,2-benziodoxol-3-(1H)-one reagent towards the synthesis of cyanamides e.g., Pyrrolidine-1-carbonitrile was disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex mols.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

HPLC of Formula: 707-61-9. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis. Author is Marsden, Stephen P.; McGonagle, Alison E.; McKeever-Abbas, Ben.

The first examples of heterocycle synthesis by iminophosphorane formation/intramol. aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. E.g., in presence of phospholene oxide I, reaction of isocyanate 2-OCNC6H4C6H4CO2Me-2, formed from acyl azide 2-N3COC6H4C6H4CO2Me-2 by Curtius rearrangement, gave 71% phenanthridine II. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ IR spectroscopy.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Synthesis of C-mannosylated glycopeptides enabled by Ni-catalyzed photoreductive cross-coupling reactions, the main research direction is mannosylated glycopeptide synthesis solvent effect; nickel catalyzed photoreductive cross coupling reaction mechanism anomerization; insect hormone solid phase peptide syntheses glycopeptide epitope antibody.Category: dioxole.

The biol. functions of tryptophan C-mannosylation are poorly understood, in part, due to a dearth of methods for preparing pure glycopeptides and glycoproteins with this modification. To address this issue, efficient and scalable methods are required for installing this protein modification. Here, we describe unique Ni-catalyzed cross-coupling conditions that utilize photocatalysis or a Hantzsch ester photoreductant to couple glycosyl halides with (hetero)aryl bromides, thereby enabling the α-C-mannosylation of 2-bromo-tryptophan, peptides thereof, and (hetero)aryl bromides more generally. We also report that 2-(α-D-mannopyranosyl)-L-tryptophan undergoes facile anomerization in the presence of acid: something that must be considered when preparing and handling peptides with this modification. These developments enabled the first automated solid-phase peptide syntheses of C-mannosylated glycopeptides, which we used to map the epitope of an antibody, as well as providing the first verified synthesis of Carmo-HrTH-I, a C-mannosylated insect hormone. To complement this approach, we also performed late-stage tryptophan C-mannosylation on a diverse array of peptides, demonstrating the broad scope and utility of this methodol. for preparing glycopeptides.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem