4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

Base Information

Chemical Name:4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal
CAS No.:1333237-32-3
Molecular Formula:C₁₈H₂₃Cl₃O₄
Molecular Weight:409.737
Hs Code.:

Synonyms:4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

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Chemical Property of 4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

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Technology Process of 4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

There total 14 articles about 4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal 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: 97.0%

: 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

: 1333237-32-3
4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1.08333h; 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

: 1333237-32-3
4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

Guidance literature:: Multi-step reaction with 4 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

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

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1002/anie.201102521

Reference yield:

: 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

: 1333237-32-3
4-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-4,4-dichlorobutanal

Guidance literature:: Multi-step reaction with 2 steps

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

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

With tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Dess-Martin oxidation;
DOI:10.1002/anie.201102521