(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

Base Information

Chemical Name:(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one
CAS No.:1258861-70-9
Molecular Formula:C₂₆H₃₁NO₄S
Molecular Weight:453.602
Hs Code.:

Synonyms:(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

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Chemical Property of (2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

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Technology Process of (2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

There total 3 articles about (2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-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: 85.0%

: 1258861-69-6
C₁₃H₁₆O₂

: 334968-78-4
(R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one

: 1258861-70-9
(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

Guidance literature:: (R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h;

C₁₃H₁₆O₂; In dichloromethane; at -78 ℃;
DOI:10.1002/cjoc.201090280

Reference yield:

: 321921-74-8
C₁₃H₁₆O₂

: 1258861-70-9
(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

3.1: titanium tetrachloride / dichloromethane / 0.25 h / -78 °C

3.2: 0.5 h / -78 °C

3.3: -78 °C

With oxalyl dichloride; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; cyclohexane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.3: Aldol condensation;
DOI:10.1002/cjoc.201090280

Reference yield:

: 321921-75-9
(2R,3R)-2-methyl-3-phenylmethoxy-4-penten-1-ol

: 1258861-70-9
(2S,3R,4S,5S)-5-benzyloxy-1-[(4R)-4-benzyl-2-thioxo-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-hept-6-en-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

2.1: titanium tetrachloride / dichloromethane / 0.25 h / -78 °C

2.2: 0.5 h / -78 °C

2.3: -78 °C

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; In dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.3: Aldol condensation;
DOI:10.1002/cjoc.201090280