Category: 93379-49-8

Rearrangement of Homoallylic Alcohols Induced by DAST was written by Canova, Sophie;Bellosta, Veronique;Mignani, Serge;Bigot, Antony;Cossy, Janine. And the article was included in Organic Letters in 2006.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

Nonracemic α-substituted-β-methoxy homoallylic alcs. RCH(OH)CH(OMe)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; TBDPS = Me₃CSi(Ph)₂; (I)] undergo diethylaminosulfur trifluoride (DAST)-mediated fluorination and rearrangement on silica gel to provide β,γ-unsaturated aldehydes RCH(CHO)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; (II)] in 76-90% yields and with good transfer of chirality. II are unstable to prolonged treatment with silica gel, rearranging to the corresponding α,β-unsaturated aldehydes, and are reduced with sodium borohydride to the primary homoallylic alcs. RCH(CH₂OH)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂]. The racemic homoallylic alcs. PhCH₂CH(OH)CH₂CH:CH₂ and TBDPSOCH₂CH₂CH(OH)CH₂CH:CH₂ lacking an α-methoxy substituent undergo fluorination without rearrangement; reaction of the secondary alc. derived from I [R = (R)-TBDPSOCH₂CHMe] by hydrogenation of the olefin with DAST yields a complex mixture In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Rearrangement of Homoallylic Alcohols Induced by DAST was written by Canova, Sophie;Bellosta, Veronique;Mignani, Serge;Bigot, Antony;Cossy, Janine. And the article was included in Organic Letters in 2006.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

Nonracemic α-substituted-β-methoxy homoallylic alcs. RCH(OH)CH(OMe)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; TBDPS = Me₃CSi(Ph)₂; (I)] undergo diethylaminosulfur trifluoride (DAST)-mediated fluorination and rearrangement on silica gel to provide β,γ-unsaturated aldehydes RCH(CHO)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; (II)] in 76-90% yields and with good transfer of chirality. II are unstable to prolonged treatment with silica gel, rearranging to the corresponding α,β-unsaturated aldehydes, and are reduced with sodium borohydride to the primary homoallylic alcs. RCH(CH₂OH)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂]. The racemic homoallylic alcs. PhCH₂CH(OH)CH₂CH:CH₂ and TBDPSOCH₂CH₂CH(OH)CH₂CH:CH₂ lacking an α-methoxy substituent undergo fluorination without rearrangement; reaction of the secondary alc. derived from I [R = (R)-TBDPSOCH₂CHMe] by hydrogenation of the olefin with DAST yields a complex mixture In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Stereoselective synthesis of amino acid-derived β-lactams. Experimental evidence for TADDOL as a memory of chirality enhancer was written by Bonache, M. Angeles;Lopez, Pilar;Martin-Martinez, Mercedes;Garcia-Lopez, M. Teresa;Cativiela, Carlos;Gonzalez-Muniz, Rosario. And the article was included in Tetrahedron in 2006.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

In model experiments, concerning the modulation of memory of chirality during the intramol. alkylation of N-(4-methoxybenzyl)-N-chloroacetyl-Phe-O-tert-Bu derivative to the corresponding β-lactam I, TADDOL was selected from a panel of different phase-transfer catalysts as the best chiral additive (ee up to 82%). We have demonstrated here that the degree and sign of the cyclization selectivity was virtually independent on TADDOL configuration, providing exptl. proof that in this reaction this additive works as a memory of chirality enhancer and not as a real catalyst. The effect of TADDOL is strongly dependent on the starting amino acid derivative, the increase of selectivity being only observed for those with aromatic side chains. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Massive Parallel Catalyst Screening: Toward Asymmetric MCRs was written by Kusebauch, Ulrike;Beck, Barbara;Messer, Kim;Herdtweck, Eberhardt;Doemling, Alexander. And the article was included in Organic Letters in 2003.Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

Hundreds of Lewis acid/ligand combinations have been screened for stereochem. induction in the Passerini multicomponent reaction. The combination of titanium tetraisopropoxide and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane was found to give enantiomeric excesses between 32% and 42% in several examples. The absolute stereo induction in the reaction of benzyl isocyanide, isobutyric aldehyde and benzoic acid with formation of amido ester PhCH₂NHCOCH(CHMe₂)OCOPh was determined chem. and by X-ray crystallog. This comprises the first asym. Passerini reaction and the first example of a stereochem. induction in an isocyanide-based multicomponent reaction by a chiral Lewis acid. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Enantioselective allylation of aldehydes with chiral allyl organolanthanide reagents was written by Qian, Chang-Tao;Huang, Tai-Sheng. And the article was included in Chinese Journal of Chemistry in 1998.Formula: C31H30O4 This article mentions the following:

The first example of enantioselective allylation of aldehydes with chiral allyl organolanthanide reagents has been achieved in high chem. yield and moderate optical purity (up to 54% e.e.). E.g., allylation of PhCHO with BrMgCH₂CH:CH₂ in presence of CeCl₃ and (+)-α,α,α’,α’-tetrakis(o-methoxyphenyl)dioxolane-4,5-dimethanol gave 71% (R)-1-phenyl-3-buten-1-ol with 54% e.e. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Formula: C31H30O4).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Formula: C31H30O4

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

Enantioselective catalytic diamination of alkenes with a bisimidoosmium oxidant was written by Muniz, Kilian;Nieger, Martin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.HPLC of Formula: 93379-49-8 This article mentions the following:

An enantioselective catalytic diamination of olefins has been developed which employs enantiopure titanium complexes as catalysts and bis(tert-butylimido)dioxoosmium(VIII) as nitrogen source. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8HPLC of Formula: 93379-49-8).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.HPLC of Formula: 93379-49-8

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

Synthesis of a Platform To Access Bistramides and Their Analogues was written by Commandeur, Malgorzata;Commandeur, Claude;Cossy, Janine. And the article was included in Organic Letters in 2011.Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

The platform C14-C40 (I), which can be used to prepare bistramide C and 39-oxobistramide K, was synthesized in 19 steps with an overall yield of 6.2%. Furthermore, the chemoselective reduction of the ketone at C-39 was performed giving an easy access to bistramides A, B, D, K, and L. Finally, the versatility of the synthesis of the C14-C40 fragment can allow the preparation of a large variety of stereoisomers to produce bistramide analogs. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Safety of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Rearrangement of Homoallylic Alcohols Induced by DAST was written by Canova, Sophie;Bellosta, Veronique;Mignani, Serge;Bigot, Antony;Cossy, Janine. And the article was included in Organic Letters in 2006.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:

Nonracemic α-substituted-β-methoxy homoallylic alcs. RCH(OH)CH(OMe)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; TBDPS = Me₃CSi(Ph)₂; (I)] undergo diethylaminosulfur trifluoride (DAST)-mediated fluorination and rearrangement on silica gel to provide β,γ-unsaturated aldehydes RCH(CHO)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; (II)] in 76-90% yields and with good transfer of chirality. II are unstable to prolonged treatment with silica gel, rearranging to the corresponding α,β-unsaturated aldehydes, and are reduced with sodium borohydride to the primary homoallylic alcs. RCH(CH₂OH)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂]. The racemic homoallylic alcs. PhCH₂CH(OH)CH₂CH:CH₂ and TBDPSOCH₂CH₂CH(OH)CH₂CH:CH₂ lacking an α-methoxy substituent undergo fluorination without rearrangement; reaction of the secondary alc. derived from I [R = (R)-TBDPSOCH₂CHMe] by hydrogenation of the olefin with DAST yields a complex mixture In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application In Synthesis of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

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

Enantioselective syntheses with titanium carbohydrate complexes. Part 7. Enantioselective allyltitanation of aldehydes with cyclopentadienyldialkoxyallyltitanium complexes was written by Hafner, Andreas;Duthaler, Rudolf O.;Marti, Roger;Rihs, Grety;Rothe-Streit, Petra;Schwarzenbach, Franz. And the article was included in Journal of the American Chemical Society in 1992.Reference of 93379-49-8 This article mentions the following:

The preparation, anal., and reactions of novel, highly stereoselective cyclopentadienyldialkoxyallyltitanium reagents, available in both enantiomeric forms, are described. Chiral monochlorotitanates are readily prepared from CpTiCl₃ (Cp = cyclopentadienyl) or Cp^*TiCl₃ (Cp^* = pentamethylcyclopentadienyl) and chiral 1,4-diols, which in turn are obtained from tartrate ester acetals by Grignard addition The resulting stable seven-membered titanacycles have been analyzed by ¹H, ¹³C, and ⁴⁹Ti NMR spectroscopy. The structures of two representatives, the complexes I (R = Cl, R¹ = Ph, Me), are confirmed by x-ray diffraction. The allyl reagents are obtained from the chlorides by transmetalation with allyllithium, allylpotassium, or allyl Grignard compounds These reagents do not have to be isolated or purified for the ensuing reactions with aldehydes. Correlation of x-ray data and Ti NMR line widths with selectivity suggests that asym. distortion of the titanium coordination geometry could be essential for enantioface discrimination, rather than direct interactions of reactants with the chiral ligand. By variation of the ligand substituents, allyltitanates derived from chloride I (R = Cl, R¹ = Ph) (with 2,2-dimethyl-α,α,α’,α’-tetraphenyl-1,3-dioxolane-3,4-dimethanol as the ligand) emerged as the most selective reagents. Excellent regio-, diastereo-, and enantioselectivities (usually ≥95% ee, ≥95% de) are obtained for reactions with various achiral and chiral aldehydes. The NMR spectra of the allyl and the crotyl complexes (R,R)-I (R = allyl, 2-butenyl, R¹ = Ph) exhibit fast 1,3-shifts favoring the (E) isomer with titanium η¹-bound to the unsubstituted allyl terminus. This equilibration, and also the equilibrations of other aryl-, alkoxy-, and silyl-substituted allyltitanium complexes, restricts this method to the preparation of branched regioisomers with the anti configuration. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Reference of 93379-49-8).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Reference of 93379-49-8

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

Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne was written by Liu, Qi-Sheng;Wang, De-Yin;Yang, Zhi-Jun;Luan, Yu-Xin;Yang, Jin-Fei;Li, Jiang-Fei;Pu, You-Ge;Ye, Mengchun. And the article was included in Journal of the American Chemical Society in 2017.Product Details of 93379-49-8 This article mentions the following:

A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes was developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an efficient strategy for the C-C bond cleavage of unreactive cyclopropanes. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Product Details of 93379-49-8).

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Product Details of 93379-49-8

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