(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

Base Information

Chemical Name:(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene
CAS No.:943981-30-4
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

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Chemical Property of (3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

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Technology Process of (3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

There total 5 articles about (3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene 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: 94.0%

: 943981-27-9
(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-5-methylhex-1-en-4-ol

: 625-45-6
2-methoxyacetic acid

: 943981-30-4
(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/jo070624o

Reference yield:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 943981-30-4
(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / iodotrimethylsilane; CrCl₂ / CH₂Cl₂ / 6 h / -42 °C

2: 94 percent / DMAP; DCC / CH₂Cl₂

With chromium dichloride; dmap; trimethylsilyl iodide; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/jo070624o

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 943981-30-4
(3S,4R,5S)-6-[(tert-butyldiphenyl)silyloxy]-3-methoxy-4-methoxyacetoxy-5-methylhex-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / Dibal-H / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3: 60 percent / iodotrimethylsilane; CrCl₂ / CH₂Cl₂ / 6 h / -42 °C

4: 94 percent / DMAP; DCC / CH₂Cl₂

With chromium dichloride; dmap; oxalyl dichloride; trimethylsilyl iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; 2: Swern oxidation;
DOI:10.1021/jo070624o