(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

Base Information

Chemical Name:(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one
CAS No.:308357-54-2
Molecular Formula:C₂₅H₄₂O₄SSi
Molecular Weight:466.758
Hs Code.:

Synonyms:(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

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Chemical Property of (+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

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Technology Process of (+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

There total 6 articles about (+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-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: 87.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 308357-53-1
(5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

: 308357-54-2
(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 3h;
DOI:10.1021/jo0007480

Reference yield:

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

: 308357-54-2
(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

Guidance literature:: Multi-step reaction with 2 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

With 2,6-dimethylpyridine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0007480

Reference yield:

: 121587-29-9
(3S)-3-methyl-1-phenylsulfonylbutan-4-ol

: 308357-54-2
(+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / 0.17 h / -78 °C

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

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

3.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo0007480