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

Base Information

Chemical Name:(5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one
CAS No.:308357-53-1
Molecular Formula:C₁₉H₂₈O₄S
Molecular Weight:352.495
Hs Code.:

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

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Chemical Property of (5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

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Technology Process of (5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one

There total 4 articles about (5R,6S,7S)-6-hydroxy-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:

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

: 308357-64-4
(2S)-2-methyl-4-(phenylsulfonyl)butanal

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

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

Guidance literature:: 3,3-dimethyl-4-oxohex-1-ene; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.416667h;

(2S)-2-methyl-4-(phenylsulfonyl)butanal; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Further stages.;
DOI:10.1021/jo0007480

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 263900-30-7
(-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

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

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

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

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;
DOI:10.1021/jo0007480