(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:160423-36-9
Molecular Formula:C₂₀H₂₇NO₄S
Molecular Weight:377.505
Hs Code.:

Synonyms:(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-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: 75.0%

: 107210-09-3
<(dimethyl-1',1' ethyl)thio>-3 propenal trans

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

: 160423-36-9
(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo00104a001

Reference yield:

: 160423-36-9
(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: (E)-(2R,3S,6R)-3-tert-Butylsulfanyl-2,6-dimethyl-7-trityloxy-hept-4-enoic acid methylamide

Guidance literature:: Multi-step reaction with 6 steps

1: PhCH₂OLi / tetrahydrofuran / 0 °C

2: DIBAL / tetrahydrofuran / -78 °C

3: DMAP, Et₃N / CH₂Cl₂

5: 92 percent / LDA, TBSCl / 1.) THF, -78 deg C, 2.) HMPA, -78 to 65 deg C

6: N,N-carbonyldiimidazole

With dmap; lithium benzyloxide; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00104a001

Reference yield:

: 160423-36-9
(4R,5S)-3-((E)-(2R,3R)-5-tert-Butylsulfanyl-3-hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: (2E,7E)-(5R,6S,9R)-6-tert-Butylsulfanyl-3,5,9-trimethyl-10-trityloxy-deca-2,7-dien-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1: PhCH₂OLi / tetrahydrofuran / 0 °C

2: DIBAL / tetrahydrofuran / -78 °C

3: DMAP, Et₃N / CH₂Cl₂

5: 92 percent / LDA, TBSCl / 1.) THF, -78 deg C, 2.) HMPA, -78 to 65 deg C

6: N,N-carbonyldiimidazole

7: t-BuLi / diethyl ether / -78 - -40 °C

8: 80 percent / NaBH₄, CeCl₃ / dimethylsulfoxide

With dmap; sodium tetrahydroborate; cerium(III) chloride; lithium benzyloxide; tert.-butyl lithium; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00104a001