(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

Base Information

Chemical Name:(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one
CAS No.:888488-42-4
Molecular Formula:C₂₅H₄₂O₅Si
Molecular Weight:450.691
Hs Code.:

Synonyms:(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

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Chemical Property of (2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

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Technology Process of (2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

There total 4 articles about (2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-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: 77.0%

: 116660-67-4,122330-69-2,149250-62-4,97848-38-9
(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal

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

: 888488-42-4
(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

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

(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal; In diethyl ether; at -78 - -23 ℃; for 16h;
DOI:10.1021/ol060347s

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 888488-42-4
(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: LiBH₄ / tetrahydrofuran / 24 h / -78 - 20 °C

2.2: 462 mg / NaIO₄ / methanol; H₂O / 0.17 h / 20 °C

3.1: dicyclohexylboron chloride; Me₂NEt / diethyl ether / -78 - 0 °C

3.2: 77 percent / diethyl ether / 16 h / -78 - -23 °C

With 2,6-dimethylpyridine; lithium borohydride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 3.2: aldol reaction;
DOI:10.1021/ol060347s

Reference yield:

: 167842-02-6
(2S,4R,5R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptan-3-one

: 888488-42-4
(2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiBH₄ / tetrahydrofuran / 24 h / -78 - 20 °C

1.2: 462 mg / NaIO₄ / methanol; H₂O / 0.17 h / 20 °C

2.1: dicyclohexylboron chloride; Me₂NEt / diethyl ether / -78 - 0 °C

2.2: 77 percent / diethyl ether / 16 h / -78 - -23 °C

With lithium borohydride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In tetrahydrofuran; diethyl ether; 2.2: aldol reaction;
DOI:10.1021/ol060347s