(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

Base Information

Chemical Name:(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol
CAS No.:1315500-60-7
Molecular Formula:C₃₁H₄₄O₄Si
Molecular Weight:508.773
Hs Code.:

Synonyms:(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

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Chemical Property of (4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

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Technology Process of (4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

There total 4 articles about (4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-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: 76.0%

: 1315500-59-4
(2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal

: 24850-33-7
allyltributylstanane

: 1315500-60-7
(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

Guidance literature:: allyltributylstanane; With indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; dichloromethane; for 0.333333h; Inert atmosphere;

(2R,3S,4R)-3-tert-butyldiphenylsilyloxy-4,5-cyclohexylidenedioxy-2-methylpentanal; In tetrahydrofuran; dichloromethane; water; at 20 ℃; for 36h; optical yield given as %de; diastereoselective reaction;
DOI:10.1055/s-0030-1260014

Reference yield:

: 1234580-28-9
(3S,4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-cyclohexylidenedioxy-3-methylhex-1-ene

: 1315500-60-7
(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: ozone / dichloromethane / 1 h / -78 °C

1.2: 16 h / 20 °C / Inert atmosphere

2.1: indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol / tetrahydrofuran; dichloromethane / 0.33 h / Inert atmosphere

2.2: 36 h / 20 °C

With indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-0030-1260014

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1315500-60-7
(4S,5S,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-cyclohexylidenedioxy-5-methyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 25 °C

2.1: ozone / dichloromethane / 1 h / -78 °C

2.2: 16 h / 20 °C / Inert atmosphere

3.1: indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol / tetrahydrofuran; dichloromethane / 0.33 h / Inert atmosphere

3.2: 36 h / 20 °C

With 1H-imidazole; indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-0030-1260014