(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

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Chemical Name:(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one
CAS No.:958461-29-5
Molecular Formula:C₃₀H₃₇NO₅S
Molecular Weight:523.693
Hs Code.:

Synonyms:(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

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Chemical Property of (2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

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Technology Process of (2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

There total 5 articles about (2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-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: 70.0%

: 872831-32-8
(1R,4S)-2-(1-benzyloxymethyl-3-methylbut-3-enyloxy)-1-(4-benzyl-2-thioxooxazo-lidin-3-yl)-ethanone

: 2100-17-6
4-pentenal

: 958461-29-5
(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

Guidance literature:: (1R,4S)-2-(1-benzyloxymethyl-3-methylbut-3-enyloxy)-1-(4-benzyl-2-thioxooxazo-lidin-3-yl)-ethanone; With titanium tetrachloride; diisopropylamine; In dichloromethane; at -78 ℃; for 2.5h;

4-pentenal; With 1-methyl-pyrrolidin-2-one; In dichloromethane; at -78 - -40 ℃; for 3h;
DOI:10.1021/ja056921x

Reference yield: 70.0%

: 872831-32-8
(1R,4S)-2-(1-benzyloxymethyl-3-methylbut-3-enyloxy)-1-(4-benzyl-2-thioxooxazo-lidin-3-yl)-ethanone

: 2100-17-6
4-pentenal

: 958461-29-5
(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

: 2-((R)-1-benzyloxymethyl-3-methylbut-3-enyloxy)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxyhept-6-en-1-one

Guidance literature:: With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -40 ℃; for 3h;
DOI:10.1021/jo0712695

Reference yield:

: 872831-42-0
(2R)-(1-benzyloxymethyl-3-methylbut-3-enyloxy)-acetic acid

: 958461-29-5
(2S,3R)-2-[(R)-1-benzyloxymethyl-3-methylbut-3-enyloxy]-1-[(S)-4-benzyl-2-thioxooxazolidin-3-yl]-3-hydroxyhept-6-en-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

2.1: titanium tetrachloride; N,N-diisopropylamine / CH₂Cl₂ / 2.5 h / -78 °C

2.2: 70 percent / N-methylpyrrolidinone / CH₂Cl₂ / 3 h / -78 - -40 °C

With dmap; titanium tetrachloride; diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/ja056921x