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

Base Information

Chemical Name: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
CAS No.:1333237-34-5
Molecular Formula:C₂₀H₂₇Cl₃O₄
Molecular Weight:437.791
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 16 articles about 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 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: 96.0%

: 1333237-33-4
methyl (Z)--((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-6,6-dichlorohex-2-enoate

: 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

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jacs.9b05013

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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

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

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

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

7.2: 0.5 h / -78 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; zirconium(IV) chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation / 6.1: Still-Gennari olefination / 6.2: Still-Gennari olefination;
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

: 1333237-34-5
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

Guidance literature:: Multi-step reaction with 6 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

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

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

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

6.2: 0.5 h / -78 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation / 5.1: Still-Gennari olefination / 5.2: Still-Gennari olefination;
DOI:10.1002/anie.201102521