(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Base Information

Chemical Name:(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate
CAS No.:261968-17-6
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

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Chemical Property of (2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

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Technology Process of (2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

There total 7 articles about (2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate 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: 98.0%

: 104701-87-3
(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: 261968-17-6
(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Guidance literature:: (S)-2-benzoyloxypentan-3-one; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; at -78 - 0 ℃; Inert atmosphere;

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal; In diethyl ether; at -78 - 0 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo9012833

Reference yield:

: C₃₄H₅₇BO₅Si

: 261968-17-6
(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Guidance literature:: With water; dihydrogen peroxide; In methanol; at 0 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(20000117)39:2<377::AID-ANIE377>3.0.CO;2-E

Reference yield:

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: 261968-17-6
(2S,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Me₂NEt / diethyl ether / 1.5 h / 0 °C

2.1: diethyl ether / 19 h / -78 - -20 °C

2.2: 99 percent / 30 percent aq. hydrogen peroxide / methanol / 0 - 20 °C / pH 7

With N,N-dimethyl-ethanamine; In diethyl ether;
DOI:10.1021/ja011211m