3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

Base Information

Chemical Name:3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one
CAS No.:618880-14-1
Molecular Formula:C₂₀H₂₀N₂O₅
Molecular Weight:368.389
Hs Code.:

Synonyms:3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

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Chemical Property of 3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

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Technology Process of 3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

There total 2 articles about 3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]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:

: 618880-06-1
(S)-3-but-2-ynyl-4-hydroxymethyl-oxazolidin-2-one

: [2-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-triphenyl-phosphonium; bromide

: 3-but-2-ynyl-4(R)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

: 618880-14-1
3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

: 3-but-2-ynyl-4-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

Guidance literature:: (S)-3-but-2-ynyl-4-hydroxymethyl-oxazolidin-2-one; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -20 ℃; for 2.5h;

[2-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-triphenyl-phosphonium; bromide; With dmap; In dichloromethane; at -20 - 0 ℃; for 1.5h;
DOI:10.1021/ol0355783

Reference yield:

: 618880-21-0
(R)-3-but-2-ynyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester

: 618880-14-1
3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / NaBH₄ / ethanol / 2 h / 0 - 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 - -20 °C

2.2: DMAP / CH₂Cl₂ / 1.5 h / -20 - 0 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 2.1: Swern oxidation / 2.2: Wittig olefination;
DOI:10.1021/ol0355783

Reference yield:

: (S)-triisopropyl-(2-methyl-pent-4-ynyloxy)-silane

: 618880-14-1
3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one

: 7-[2-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-2-oxoethyl]-6-[1,5(S)-dimethyl-6-(triisopropyl-silanyloxy)-hex-2-enylidene]-2(S),3(S)-tetrahydro-pyrrolo[1,2-c]oxazol-2-one

Guidance literature:: (S)-triisopropyl-(2-methyl-pent-4-ynyloxy)-silane; With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 0.5h;

With zinc(II) chloride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

3-but-2-ynyl-4(S)-[3-(4(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propenyl]oxazolidin-2-one; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ol0355783