(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one
CAS No.:354816-58-3
Molecular Formula:C₃₁H₂₈NO₃PS
Molecular Weight:525.608
Hs Code.:

Synonyms:(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

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Chemical Property of (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

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Technology Process of (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

There total 5 articles about (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-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: 44.6%

: 55905-05-0
diphenylphosphine sulphide

: 128891-66-7
(4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

: 354816-58-3
(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

: 354816-57-2
(4S)-4-benzyl-3-[(3S)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/jo049103g

Reference yield:

: 3282-30-2
pivaloyl chloride

: 101711-90-4,123731-35-1,128677-61-2
(S)-4-benzyl-2-oxazolidinone lithium salt

: 192371-81-6
3-(Diphenyl-phosphinothioyl)-3-phenyl-propionic acid

: 354816-58-3
(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

: 354816-57-2
(4S)-4-benzyl-3-[(3S)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

Guidance literature:: pivaloyl chloride; 3-(Diphenyl-phosphinothioyl)-3-phenyl-propionic acid; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 1.5h;

(S)-4-benzyl-2-oxazolidinone lithium salt; In tetrahydrofuran; hexane; at 0 ℃; for 2h; Further stages.;
DOI:10.1021/ol0161256

Reference yield:

: 829-85-6
diphenylphosphane

: 354816-58-3
(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 3 h / -78 - 25 °C

1.2: n-BuLi / tetrahydrofuran / 16 h

1.3: Na₂S₂O₃ / H₂O; tetrahydrofuran / 8 h

2.1: DIPEA / tetrahydrofuran / 1.5 h / 0 °C

2.2: 2.08 g / tetrahydrofuran; hexane / 2 h / 0 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/ol0161256