(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

Base Information

Chemical Name:(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol
CAS No.:1333237-36-7
Molecular Formula:C₂₀H₂₈Cl₄O₅
Molecular Weight:490.251
Hs Code.:

Synonyms:(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

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Chemical Property of (2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

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Technology Process of (2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

There total 10 articles about (2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 1333237-35-6
((2S,3R)-3-(3-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,3-dichloropropyl)oxiran-2-yl)methanol

: 1333237-36-7
(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

: C₂₀H₂₈Cl₄O₅

Guidance literature:: With magnesium chloride; In ethyl acetate; at 80 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1021/jacs.9b05013

Reference yield: 40.0%

: (3-(3-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,3-dichloropropyl)oxiran-2-yl)methanol

: C₂₀H₂₈Cl₄O₅

: 1333237-36-7
(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

Guidance literature:: (3-(3-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,3-dichloropropyl)oxiran-2-yl)methanol; With triisopropoxytitanium(IV) chloride; In hexane; benzene; at 20 ℃; for 14h; Inert atmosphere;

With tartaric acid; In hexane; benzene; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/anie.201102521

Reference yield:

: 1333237-27-6
1-((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)-5-((tert-butyldiphenylsilyl)oxy)-2,2-dichloropentan-1-one

: 1333237-36-7
(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

: C₂₀H₂₈Cl₄O₅

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetrachlorosilane; N,N,N,N,N,N-hexamethylphosphoric triamide / dichloromethane / 96 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; acetic acid / acetonitrile / 1 h / 0 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 25 h / 0 - 20 °C / Inert atmosphere

4.1: tetra-n-butylammoniumfluoride trihydrate; acetic acid / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere

6.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere

6.2: 0.25 h / -78 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

8.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tert.-butylhydroperoxide / dichloromethane; decane / 24 h / -20 °C / Molecular sieve; Inert atmosphere

9.1: magnesium chloride / ethyl acetate / 0.08 h / 80 °C / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; tetrachlorosilane; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; tetra-n-butylammoniumfluoride trihydrate; magnesium chloride; In tetrahydrofuran; decane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: |Dess-Martin Oxidation / 6.1: |Still-Gennary Z-Olefination / 6.2: |Still-Gennary Z-Olefination / 8.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jacs.9b05013