((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

Base Information

Chemical Name:((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
CAS No.:1333237-35-6
Molecular Formula:C₂₀H₂₇Cl₃O₅
Molecular Weight:453.79
Hs Code.:

Synonyms:((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

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Chemical Property of ((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

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Technology Process of ((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

There total 22 articles about ((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 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:

: 1333237-34-5
methyl (Z)--((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-6,6-dichlorohex-2-en-1-ol

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

: 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

Guidance literature:: methyl (Z)--((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-6,6-dichlorohex-2-en-1-ol; With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With tert.-butylhydroperoxide; In nonane; dichloromethane; at -20 ℃; for 24.25h; optical yield given as %de; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1002/anie.201102521

Reference yield:

: 1333237-28-7
(2S,3S)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-3,5,5-trichloro-2-hydroxyoctan-4-one

: 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

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

5.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere

5.2: 0.25 h / -78 °C / Inert atmosphere

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

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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; tetra-n-butylammoniumfluoride trihydrate; In tetrahydrofuran; decane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: |Dess-Martin Oxidation / 5.1: |Still-Gennary Z-Olefination / 5.2: |Still-Gennary Z-Olefination / 7.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jacs.9b05013

Reference yield:

: 1333237-31-2
4-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutan-1-ol

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

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

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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; decane; dichloromethane; toluene; 1.1: |Dess-Martin Oxidation / 2.1: |Still-Gennary Z-Olefination / 2.2: |Still-Gennary Z-Olefination / 4.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jacs.9b05013