(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

Base Information

Chemical Name:(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one
CAS No.:688334-09-0
Molecular Formula:C₃₃H₅₆O₄Si
Molecular Weight:544.891
Hs Code.:

Synonyms:(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

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Chemical Property of (2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

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Technology Process of (2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

There total 6 articles about (2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 688334-04-5
(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-hydroxy-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

: 688334-09-0
(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1.25h;
DOI:10.1021/ol0497483

Reference yield:

: 174627-66-8
(2S,4S,6S)-2,4,6-trimethyl-1-nonanal

: 688334-09-0
(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: s-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

1.2: tetrahydrofuran; pentane / -78 - -20 °C

1.3: 0.38 g / CF₃CO₂H / tetrahydrofuran / 1.5 h / 0 °C

2.1: diethyl ether / -78 - -20 °C

2.2: 82 percent / H₂O₂ / methanol; H₂O / 1 h / 0 °C / pH 7

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

With 2,6-dimethylpyridine; sec.-butyllithium; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/ol0497483

Reference yield:

: 156162-12-8
(2E,4S,6S,8S)-2,4,6,8-tetramethyl-2-undecenal

: 688334-09-0
(2S,4R,5S,6E,8S,10S,12S)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8,10,12-pentamethyl-pentadec-6-en-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether / -78 - -20 °C

1.2: 82 percent / H₂O₂ / methanol; H₂O / 1 h / 0 °C / pH 7

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

With 2,6-dimethylpyridine; In diethyl ether; dichloromethane;
DOI:10.1021/ol0497483