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

Base Information

Chemical Name:4-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutan-1-ol
CAS No.:1333237-31-2
Molecular Formula:C₁₈H₂₅Cl₃O₄
Molecular Weight:411.753
Hs Code.:

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

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

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

There total 13 articles about 4-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutan-1-ol 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: 100.0%

: 1333237-30-1
(4-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutoxy)(tert-butyl)diphenylsilane

: 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

Guidance literature:: With acetic acid; tetra-n-butylammoniumfluoride trihydrate; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jacs.9b05013

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

1.2: 0.17 h / -78 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
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

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

1.2: 0.08 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; zirconium(IV) chloride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.201102521