(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

Base Information

Chemical Name:(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone
CAS No.:1330064-18-0
Molecular Formula:C₂₄H₂₂O₄S
Molecular Weight:406.502
Hs Code.:

Synonyms:(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

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Chemical Property of (2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

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Technology Process of (2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

There total 3 articles about (2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone 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: 85.0%

: 41024-57-1
1-([1,1’-biphenyl]-4-yl)-2-(phenylsulfonyl)ethanone

: 123-73-9,4170-30-3
crotonaldehyde

: 1330064-18-0
(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

Guidance literature:: 1-([1,1’-biphenyl]-4-yl)-2-(phenylsulfonyl)ethanone; crotonaldehyde; With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; In chloroform; at -35 ℃; for 24h;

With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; potassium acetate; In chloroform; at -35 - 20 ℃; for 24h; optical yield given as %ee; stereoselective reaction;
DOI:10.1002/ejoc.201100690

Reference yield:

: 135-73-9
2-Bromo-4'-phenylacetophenone

: 1330064-18-0
(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / 24 h / 20 °C

2.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / chloroform / 24 h / -35 °C

2.2: 24 h / -35 - 20 °C

With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; In chloroform; N,N-dimethyl-formamide; 2.1: Michael addition / 2.2: Benzoin condensation;
DOI:10.1002/ejoc.201100690

Reference yield:

: 873-55-2
sodium benzenesulfonate

: 1330064-18-0
(2R,3S,4R)-2-hydroxy-4-methyl-2-([1,1'-biphenyl]-4-yl)-3-(phenylsulfonyl)cyclopentanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / 24 h / 20 °C

2.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / chloroform / 24 h / -35 °C

2.2: 24 h / -35 - 20 °C

With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; In chloroform; N,N-dimethyl-formamide; 2.1: Michael addition / 2.2: Benzoin condensation;
DOI:10.1002/ejoc.201100690