(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

Base Information

Chemical Name:(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione
CAS No.:1309575-59-4
Molecular Formula:C₁₉H₂₃NO₄S
Molecular Weight:361.462
Hs Code.:

Synonyms:(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

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Chemical Property of (4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

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Technology Process of (4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

There total 2 articles about (4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione 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: 49.3%

: 19798-71-1
2-methyl-2-methoxy-1,3-dioxolane

: 247058-11-3
4S-1-(4-benzyl-2-thiooxazolidin-3-yl)pent-4-en-1-one

: 1309575-59-4
(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

Guidance literature:: 4S-1-(4-benzyl-2-thiooxazolidin-3-yl)pent-4-en-1-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

2-methyl-2-methoxy-1,3-dioxolane; In dichloromethane; at -78 - -20 ℃; for 1h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol200886j

Reference yield:

: 591-80-0
pent-4-enoic acid

: 131744-19-9,145588-94-9
(4S)-4-benzyl-1,3-oxazolidine-2-thione

: 1309575-59-4
(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - -20 °C / Inert atmosphere

With dmap; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/ol200886j

Reference yield:

: 1309575-59-4
(4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione

: C₂₁H₂₇NO₇

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene / 0.58 h / -78 °C / Inert atmosphere

1.2: 0.42 h / -78 - 0 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

With pyridine; diisobutylaluminium hydride; In dichloromethane; toluene;
DOI:10.1021/ol200886j