Day: November 8, 2022

Kissman, Henry M.; Baker, B. R. published an article in 1957, the title of the article was Synthesis of certain 5-deoxy-D-ribofuranosylpurines.Name: (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole And the article contains the following content:

Me 2,3-O-isopropylidene-D-ribofuranoside (I) (30.6 g.) in 90 cc. pyridine treated dropwise with stirring and cooling with 17.4 g. MeSO2Cl, kept at 5° overnight, poured into 400 cc. ice H2O, and extracted with CHCl3, the extract washed, dried, treated with C, and evaporated in vacuo, the residue dissolved in 500 cc. Et2O, the solution filtered through Norite, and the filtrate concentrated gave 26.8 g. 5-mesylate (II) of I, m. 78-9° (EtOAc-cyclohexane) (all m.ps. are corrected), [α]24D -53.0° (c 1.86, CHCl3). II (8.5 g.) in 90 cc. HCONMe2 refluxed 1.5 hrs. with stirring with 5.06 g. NaI, cooled, and filtered, the residue washed with Et2O, the combined filtrates concentrated in vacuo at 70° to about 30 cc., diluted with 300 cc. H2O, and extracted with Et2O, the extract dried, decolorized with Norite, and evaporated in vacuo, and the oily residue (8.4 g.) distilled gave 7.2 g. 5-deoxy-5-iodo analog (III) of II, b0.1 75-80°, [α]24.5D -68.6° (c 2, CHCl3). III (3.22 g.) in 30 cc. MeOH containing 1.56 cc. Et3N treated with a small piece of Dry Ice, hydrogenated over 0.322 g. 10% Pd-C, and filtered through Celite, the filtrate concentrated in vacuo at 30°, mixed with 50 cc. CH2Cl2, washed with 10 cc. H2O and 10 cc. saturated aqueous NaHCO3, dried, and evaporated in vacuo, and the residue distilled yielded 1.08 g. 5-deoxy analog (IV) of II, b20 92-5°. III (32.5 g.) in 100 cc. MeOH containing 30 cc. Et3N hydrogenated 19 min. at 35 lb. over 3 g. Raney Ni in 20 cc. MeOH, filtered, and evaporated in vacuo at room temperature, the residue triturated with Et2O and filtered to give 19.9 g. Et3N.HI, and the filtrate washed, dried, and distilled gave 13.96 g. IV, b20-25 95-9°. IV (825 mg.) and 12 cc. 0.4N HCl heated 2 hrs. on the steam bath with occasional shaking, cooled to room temperature, diluted with 40 cc. H2O, neutralized with Duolite A-4 resin (OH form), and filtered, the filtrate evaporated in vacuo at 50°, and the residue evaporated twice with C6H6 and dried over P2O5 in vacuo yielded 575 mg. 5-deoxy-D-ribose (V), light yellow sirup. V (269 mg.) in 0.5 cc. H2O added to 396 mg. 2,4-(O2N)2C6H3-NHNH2 in 12 cc. absolute EtOH, refluxed, 12 hrs., and evaporated to dryness in vacuo gave 453 mg. 2,4-dinitrophenylhydrazone, of V, m. 151-2° (decomposition) (C6H6-CH2Cl2), [α]25D -30.2° (c 0.99, MeOH). V (575 mg.) in 20 cc. pyridine kept 3 days at room temperature with 3 cc. Ac2O, treated with 50 cc. cold saturated aqueous NaHCO3, and extracted with CHCl3, the residue from the extract evaporated with PhMe, dissolved in dry Et2O, treated with Darco, and evaporated, and the final residue (960 mg.) distilled in vacuo yielded 746 mg. 1,2,3-triacetate (VI) of V, b0.2 118-20°. IV (1.88 g.) hydrolyzed and acetylated, the Et2O solution of the product evaporated, and the residue (2.49 g.) of mixed acetates crystallized from hexane yielded 766 mg. β-anomer of VI, m. 64-5° (hexane-Et2O), [α]25D -26.9° (c 2.42, CHCl3); the mother liquor distilled gave 829 mg. oil (mainly α-VI), b0.1 100-3°, [α]25D 17.0° (c 2.71, CHCl3). Mixed VI (2.6 g.) in 80 cc. Et2O (saturated at 0° with HCl) kept 72 hrs. at -3° and evaporated in vacuo, the residual gummy 1-chloro-2,3-di-O-acetyl-5-deoxy-D-ribose (VII) dissolved in 25 cc. xylene, the solution added to a dry suspension of 6.25 g. chloromercuri-6-dimethylaminopurine-Celite (containing 3.88 g. purine derivative) in 100 cc. xylene, refluxed 3 hrs. with stirring, and filtered, the residue washed with CHCl3, the combined filtrates evaporated in vacuo, the residue dissolved in 80 cc. CHCl3 and filtered, the filtrate washed with 20 cc. 30% aqueous KI and with 20 cc. H2O, dried, clarified with Darco, filtered, and evaporated in vacuo, the residual dark yellow gum (3.14 g.) containing a maximum of 72% 2,3-diacetate (VIII) of 6-dimethylamino-9-(5-deoxy-D-ribofuranosyl)purine (IX) dissolved in 50 cc. absolute MeOH, the solution refluxed 0.5 hr. with 0.3 cc. N NaOMe-MeOH and evaporated in vacuo, and the dark residue decolorized in dry Me2CO with C and evaporated gave 771 mg. IX, m. 163-5° (iso-PrOH), [α]24.5D -50.7° (c 2.02, EtOH). VII from 1.3 g. VI in 10 cc. xylene added to 4 g. mixture of chloromercuri-6-chloropurine and Celite (2 g.) in 140 cc. xylene, refluxed 3 hrs. with stirring and processed in the usual manner gave 1.63 g. diacetate (X) of 6-chloro-9-(5-deoxy-β-D-ribofuranosyl)-purine (XI) (74% pure). VII (1.6 g.) kept 16 hrs. at -3° with 25 cc. MeOH (saturated at 3° with NH3) and evaporated in vacuo at 25°, the residue dissolved in hot EtOAc, filtered through C, and evaporated to dryness, the residue (1.03 g.) dissolved in a min. of EtOAc, and the solution seeded and diluted with C6H5 until cloudy gave 355 g. XI, m. 154-6°, [α]24D -45.5° (c 1.69, EtOH). VII from 2.60 g. VI added to 10.2 g. mixture of chloromercuri-6-benzamidopurine and Celite (containing 4.74 g. purine derivative) in 120 cc. xylene, refluxed 3 hrs. with stirring, and worked up in the usual manner, the resulting dark gummy product deacetylated in the usual manner, the product dissolved in 50 cc. MeOH, and the solution refluxed 0.5 hr. with 1 cc. N NaOMe-MeOH and evaporated in vacuo gave 1.92 g. dark gum; 1.2 g. dissolved in 60 cc. H2O, filtered, treated with Amberlite IRC-50 (H form) and then with C, and evaporated in vacuo, the residue (770 mg.) dissolved in 5 cc. H2O (saturated with EtOAc), mixed with 10 g. Celite, packed on top of a column of 230 g. Celite packed with 115 cc. H2O (saturated with EtOAc), and developed gave 183 mg. 6-amino-9-(5-deoxy-β-D-ribofuranosyl)purine (5′-deoxyadenosine) (XII), m. 210-12° after liquefaction at 180° and resolidification, [α]25D -52.7° (c 1.00, EtOH). Crude condensation product from 10 millimoles of VI refluxed 75 min. in 50 cc. MeOH containing 1 cc. N NaOMe-MeOH and evaporated in vacuo, the residue dissolved in 50% aqueous EtOH, neutralized with stirring with Amberlite IRC-50 resin, filtered, and evaporated in vacuo, the residue in 50 cc. H2O extracted with EtOAc and evaporated in vacuo, the residual glass (1.49 g.) dissolved in absolute EtOH, filtered through C, concentrated to 15 cc., seeded with XII, and the deposit washed with a little EtOH and Et2O and dried in vacuo gave 472 mg. XII, m. 205-7° with shrinking at 120 and 185°; the combined mother liquors evaporated, the residual glass dissolved in hot EtOAc-EtOH, and the solution concentrated at the b. p. gave successive fractions of gummy precipitate which crystallized from EtOH at 0° yielded 123 mg. α-anomer of XII, m. 173-5° with shrinking at 115-20°, [α]24.5D -9.9° (c 1.62, EtOH). Crude XII (1.3 g.) from a similar run (containing a maximum of 71% XII) partitioned in EtOAc-H2O on 210 g. Celite gave 279 mg. β-anomer of XII, m. 206-8° with partial melting and resolidification at 125-30°, [α]24D -26.9° (c 1.5, EtOH), 173 mg. mixture of α- and β-XII, m. unsharply at 115°, and 67 mg. solid, m. 110-15°, [α]24D 53.0° (c 0.75, EtOH). VI (0.65 g.) converted to X gave 777 mg. crude gum containing a maximum of 67% X; the gum in 25 cc. MeOH (saturated at 0° with NH3), heated 5 hrs. in a sealed tube at 100°, cooled, and evaporated in vacuo, and the residue in a small amount of hot EtOH decolorized with C and cooled yielded 141 mg. crude II, m. above 125° (unsharp), [α]24D -48.2° (c 1.02, EtOH); the mother liquor evaporated, the residue dissolved in H2O, treated with C, evaporated in vacuo, dissolved in the min. amount of EtOH, diluted to cloudiness with EtOAc, and filtered, the filtrate evaporated, the residue dissolved in the min. amount hot H2O, and the solution allowed to stand several days in an open vessel gave 88% pure XII, [α]24D -49.7° (c 0.19, EtOH); the combined crude XII recrystallized from EtOH gave 136 mg. β-XII, m. 208-9°, [α]24D -54.0° (c -54.0°) (c 0.63, EtOH). X from 1.40 g. VI in 50 cc. EtOH hydrogenated 3 hrs. at atm. pressure 367 mg. 10% Pd-C (wetted with 2 cc. Methyl Cellosolve) and 151 mg. MgO and filtered through Celite, the residue washed with EtOH, the combined filtrates evaporated in vacuo, the residue dissolved in 50 cc. CHCl3, the solution washed with H2O, dried, and evaporated in vacuo, and the residue (1.33 g.) dissolved in 20 cc. Et2O and diluted to cloudiness with hexane gave 404 mg. 9-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)purine (XIII), m. 119-20°, [α]24D -26.8° (c 1.49, EtOH). XIII (320 mg.) in 15 cc. absolute MeOH containing 0.2 cc. N NaOMe-MeOH refluxed 0.5 hr. and evaporated in vacuo, the residue dissolved in hot EtOAc containing some MeOH, filtered, and evaporated in vacuo, and the gummy residue (277 mg.) recrystallized from Et2O-CH2Cl2 yielded 60 mg. 9-(5-deoxy-β-D-ribofuranosyl)purine (5′-deoxynebularine) (XIV), m. 115-16°, [α]25D -28.3° (c 1.83, EtOH). XI (270 mg.) in 43 cc. H2O hydrogenated 75 min. with stirring at atm. pressure over 98 mg. 10% Pd-C and 40 mg. MgO, filtered through Celite, and evaporated in vacuo, the residual glass 271 mg. dissolved in hot CHCl3 containing some MeOH, cooled, filtered, and evaporated in vacuo, and the residue crystallized from Et2O-CH2Cl2 yielded 69 mg. XIV, m. 115-16°. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Name: (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

(3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas:38838-06-1) belongs to dioxoles. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Name: (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

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

On May 31, 2000, Nouguier, Robert published an article.Computed Properties of 38838-06-1 The title of the article was Synthesis of methyl esters of 6,7-dideoxy-α-D-manno (and gluco)octopyranosiduronic acids and of methyl 5,6-dideoxy-β-D-riboheptofuranosiduronic acids by one-pot two carbon extension steps. And the article contained the following:

In DMSO at 100 °C, the anion of di-Me malonate reacts with primary iodides derived from mannose, glucose and ribose. Without isolation of the di-Me sugar-malonyl derivative, addition in the same flask of NaCl and H2O and heating at 160 °C leads to the decarbomethoxylated product in good yield. This is a very simple one-pot method for 2-C extension of carbohydrates chains. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Computed Properties of 38838-06-1

The Article related to uronic acid ester synthesis malonate condensation homologation, Carbohydrates: Acids and other aspects.Computed Properties of 38838-06-1

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

On April 15, 2014, Davies, Stephen G.; Foster, Emma M.; Lee, James A.; Roberts, Paul M.; Thomson, James E. published an article.Application of 38838-06-1 The title of the article was Doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to enantiopure ε-O-protected α,β-unsaturated esters derived from D-ribose. And the article contained the following:

Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β-unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective ‘matched’ and ‘mismatched’ reaction pairings in which the inherent reagent control serves to augment or oppose, resp., the established substrate diastereo-control. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Application of 38838-06-1

The Article related to stereoselective addition lithium methylbenzylamide ribose amino acid preparation, Carbohydrates: Acids and other aspects.Application of 38838-06-1

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

On December 24, 1999, Gallos, John K.; Koumbis, Alexandros E.; Xiraphaki, Vassiliki P.; Dellios, Constantinos C.; Coutouli-Argyropoulou, Evdoxia published an article.COA of Formula: C9H15IO4 The title of the article was Diastereocontrol in the intramolecular cycloadditions of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides. And the article contained the following:

The influence of the 2-substituent on the diastereoselectivity of the intramol. cycloadditions in a series of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides, generated in situ from selected sugar derivatives, was examined in synthesis of aminocyclopentitols, e.g. I. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).COA of Formula: C9H15IO4

The Article related to stereoselective intramol cycloaddition erythrodioxyhexenenitrile synthesis aminocyclopentitol, Carbohydrates: Amines and other aspects.COA of Formula: C9H15IO4

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

On March 21, 1994, Gallos, John K.; Goga, Efthymia G.; Koumbis, Alexandros E. published an article.Formula: C9H15IO4 The title of the article was Expeditious synthesis of aminocyclopentitols from D-ribose via intramolecular nitrone cycloaddition. And the article contained the following:

The synthesis of aminocyclopentitol I (a key-intermediate in the preparation of carbocyclic nucleosides) and its N-substituted derivatives, has been achieved by the intramol. nitrone cycloadditions of a γ-unsaturated aldehyde, easily accessible from D-ribose, followed by reductive N-O bond cleavage in the resulting bicyclic oxazanes II. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Formula: C9H15IO4

The Article related to ribose conversion aminocyclopentitol, aminocyclopentitol, bicyclic oxazane preparation reductive bond cleavage, Carbohydrates: Amines and other aspects.Formula: C9H15IO4

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

On December 23, 1988, Classon, Bjoern; Liu, Zhengchun; Samuelsson, Bertil published an article.SDS of cas: 38838-06-1 The title of the article was New halogenation reagent systems useful for the mild one-step conversion of alcohols into iodides or bromides. And the article contained the following:

Three new iodination and bromination reagent systems based upon phosphines are described, in which the phosphorus containing products are readily removed from the organic phase of the reaction mixture Reactions were carried out on suitably protected carbohydrates. The halogenation reagent systems consist of iodine (or bromine), imidazole and one of the following reagents: (A); Ph2PCl, (B); (p-dimethylaminophenyl)diphenylphosphine or (C); polymer-bound triphenylphosphine. The solvent used is toluene, and the phosphorous containing products are removed from the toluene phase by extraction into an aqueous sodium carbonate or sodium hydroxide phase (A); by extraction into an aqueous hydrochloric acid (pH≈1) phase (B); and by filtration (C). Ph2PCl is com. available and halogenation reagent system (A) represents the most reactive (shorter reaction time and lower temperature), of the three systems. Yields for all systems are high. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).SDS of cas: 38838-06-1

The Article related to halogenation carbohydrate reagent system, bromination carbohydrate reagent system, iodination carbohydrate reagent system, Carbohydrates: General and other aspects.SDS of cas: 38838-06-1

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

On June 30, 2007, Shitikova, O. V.; Ivanova, N. A.; Valiullina, Z. R.; Miftakhov, M. S.; Spirikhin, L. V. published an article.Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole The title of the article was 1H NMR study on intramolecular hydrogen bonding in 2,3-O-isopropylidene-D-ribofuranosides and their 5(4)-hydroxy derivatives. And the article contained the following:

A 1H NMR study showed the possibility for intramol. hydrogen bonding in 5(4)-hydroxy derivatives of 2,3-O-isopropylidene-β-D-ribofuranose in CDCl3. The obtained data were used to interpret differences in the 1H NMR spectra of structurally related 5-halo-2,3-O-isopropylidene-D-ribofuranosides and four diastereoisomeric 5-bromo-5-deoxy-4-hydroxy-2,3-O-isopropylidene-D-ribofuranosides. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

The Article related to nmr hydrogen bond ribofuranoside, Carbohydrates: Glycosides and other aspects.Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

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

On May 21, 2008, Zhu, Renfa published a patent.Product Details of 38838-06-1 The title of the patent was Method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose. And the patent contained the following:

The title method comprises adopting D-ribose as raw material, performing glycosidation and esterification to obtain 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-D-ribofuranose, performing iodination with sodium iodide or potassium iodide to obtain 2,3-O-isopropylidene-5-iodo-5-deoxy-D-ribofuranose, performing catalytic hydrogenation to obtain 2,3-O-isopropylidene-5-deoxy-D-ribofuranose, and hydrolyzing to obtain the final product with m.p. of 62-64°C. The method has the advantages of mild reaction condition, wide raw material resources, no pollution, and high yield (37.8%). The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Product Details of 38838-06-1

The Article related to deoxyribofuranose triacetate preparation green chem, Carbohydrates: Glycosides and other aspects.Product Details of 38838-06-1

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

Soengas, Raquel G.; Silva, Artur M. S. published an article in 2013, the title of the article was Domino Reaction of Iodoglycosides: Synthesis of Carbohydrate-Based Nitroalkenes.Electric Literature of 38838-06-1 And the article contains the following content:

Herein we describe a tandem fragmentation/H reaction of iodoglycosides, which involves formation of a carbon-carbon double bond and a carbon-carbon single bond. If the fragmentation of Me 5-iodo-ribofuranoside is mediated by zinc/catalytic indium in the presence of bromonitromethane, a separable mixture of a 1-nitro-5-hexene and a 1-bromo-1-nitro-5-hexene is obtained in moderate yields with good diastereoselectivities. However, if the reaction is mediated by nBuLi in the presence of nitromethane, the corresponding 1-nitro-5-hexene is obtained as the only product in excellent yield and stereoselectivity in a one-pot synthetic protocol. This is a general methodol. that can be applied to iodopyranoses and iodofuranoses with different protecting groups for the efficient preparation of highly functionalized 1-nitro-5-hexenes or 1-nitro-6-heptenes. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Electric Literature of 38838-06-1

The Article related to carbohydrate nitroalkene preparation fragmentation henry iodoglycoside, Carbohydrates: Glycosides and other aspects.Electric Literature of 38838-06-1

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