(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

Base Information

Chemical Name:(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one
CAS No.:308357-55-3
Molecular Formula:C₃₃H₆₀O₅SSi₂
Molecular Weight:625.073
Hs Code.:

Synonyms:(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

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Chemical Property of (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

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Technology Process of (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

There total 15 articles about (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-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: 92.0%

: 3112-85-4
methylphenylsulfonate

: Toluene-4-sulfonic acid (2S,3S,4R,7S)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,6-tetramethyl-5-oxo-dec-9-enyl ester

: 308357-55-3
(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

Guidance literature:: DOI:10.1007/s007060070099

Reference yield: 78.0%

: (7R,8S,9S)-11-Benzenesulfonyl-8-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-undec-1-en-6-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 308357-55-3
(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 3h;
DOI:10.1021/jo0007480

Reference yield:

: 78186-80-8
3,3-dimethyl-4-oxohex-1-ene

: 308357-55-3
(4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; various solvent(s) / 0.42 h / -78 °C

1.2: tetrahydrofuran; various solvent(s) / 0.08 h / -78 °C

2.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -20 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 98 percent / PPh₃ / CH₂Cl₂; methanol / 3 h / -78 - 20 °C

4.1: (-)DIPCl / diethyl ether / 1.67 h / -78 - 20 °C

4.2: 52 percent / diethyl ether / 3 h / -78 °C

5.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; ozone; (-)-diisopinocamphenylborane chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.2: Brown allylation;
DOI:10.1021/jo0007480