(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

Base Information

Chemical Name:(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one
CAS No.:1259491-16-1
Molecular Formula:C₃₁H₄₈O₂Si
Molecular Weight:480.806
Hs Code.:

Synonyms:(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

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Chemical Property of (-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

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Technology Process of (-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

There total 1 articles about (-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one 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: 88.0%

: 1259491-15-0
(-)-(6R,8S,10S,E)-11-(tert-butyl-diphenyl-silyloxy)-6,8,10-trimethyl-undec-3-en-2-one

: 75-16-1
methylmagnesium bromide

: 1259491-16-1
(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

Guidance literature:: methylmagnesium bromide; With (R,S(Fe))-Josiphos/CuBr; In t-BuOMe; diethyl ether; at -80 ℃; for 0.333333h; Inert atmosphere;

(-)-(6R,8S,10S,E)-11-(tert-butyl-diphenyl-silyloxy)-6,8,10-trimethyl-undec-3-en-2-one; In t-BuOMe; diethyl ether; at -80 ℃; for 19.5h; Inert atmosphere;

With methanol; In diethyl ether; tert-butyl alcohol; at -80 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201001284

Reference yield:

: 1259491-16-1
(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

: C₃₁H₄₈O₃Si

Guidance literature:: With sodium percarbonate; trifluoroacetic anhydride; In dichloromethane; at 20 ℃;
DOI:10.1016/j.chembiol.2018.01.006

Reference yield:

: 1259491-16-1
(-)-(4R,6R,8S,10S)-11-(tert-butyl-diphenyl-silyloxy)-4,6,8,10-tetramethyl-undecan-2-one

: (2R,4R,6S,8S)-9-((tert-butyldiphenylsilyl)oxy)-2,4,6,8-tetramethylnonan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: trifluoroacetic anhydride; sodium percarbonate / dichloromethane / 20 °C

2: potassium carbonate; methanol / 3 h / 20 °C

With methanol; sodium percarbonate; potassium carbonate; trifluoroacetic anhydride; In dichloromethane; 1: |Baeyer-Villiger Ketone Oxidation;
DOI:10.1016/j.chembiol.2018.01.006