(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

Base Information

Chemical Name:(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one
CAS No.:681830-23-9
Molecular Formula:C₃₁H₄₅NO₅SSi
Molecular Weight:571.854
Hs Code.:

Synonyms:(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

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Chemical Property of (2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

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Technology Process of (2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

There total 5 articles about (2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-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: 53.0%

: 501644-56-0
(S)-2-(benzyloxy)-1-(4-benzyl-2-thioxooxazolidin-3-yl)ethanone

: 681830-17-1
(2R,4R)-2-Methyl-4-triethylsilanyloxy-pentanal

: 681830-22-8
WY₁₁₁₄₀₃

: 681830-23-9
(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

Guidance literature:: (S)-2-(benzyloxy)-1-(4-benzyl-2-thioxooxazolidin-3-yl)ethanone; With titanium tetrachloride; (-)-sparteine; In dichloromethane; at -78 ℃; for 1.5h;

(2R,4R)-2-Methyl-4-triethylsilanyloxy-pentanal; In dichloromethane; at -78 ℃; for 0.666667h;
DOI:10.1021/jo035829l

Reference yield:

: 994-30-9
triethylsilyl chloride

: 681830-23-9
(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

2.1: 78 percent / diisopropylamine; n-BuLi; BH₃*NH₃ / tetrahydrofuran; hexane / 12 h / 0 - 20 °C

3.1: 85 percent / NMO / TPAP / CH₂Cl₂ / 0.5 h

4.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 1.5 h / -78 °C

4.2: 15 percent / CH₂Cl₂ / 0.67 h / -78 °C

With dmap; n-butyllithium; borane-ammonia complex; N-methyl-2-indolinone; titanium tetrachloride; triethylamine; diisopropylamine; (-)-sparteine; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; 3.1: Ley oxidation;
DOI:10.1021/jo035829l

Reference yield:

: 681830-33-1
(2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol

: 681830-23-9
(2S,3S,4R,6R)-2-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 85 percent / NMO / TPAP / CH₂Cl₂ / 0.5 h

2.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 1.5 h / -78 °C

2.2: 15 percent / CH₂Cl₂ / 0.67 h / -78 °C

With N-methyl-2-indolinone; titanium tetrachloride; (-)-sparteine; tetrapropylammonium perruthennate; In dichloromethane; 1.1: Ley oxidation;
DOI:10.1021/jo035829l