(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one
CAS No.:519002-38-1
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

Synonyms:(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

There total 1 articles about (R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-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: 92.0%

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 104372-55-6,519002-37-0
(S)-(E)-2-methyl-hex-4-enal

: 519002-38-1
(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.75h;

(S)-(E)-2-methyl-hex-4-enal; In dichloromethane; at -78 ℃; for 5h;

With dihydrogen peroxide; In methanol; dichloromethane; at -78 - 0 ℃; for 0.666667h;
DOI:10.1021/ja021327y

Reference yield:

: 519002-38-1
(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

: 519002-51-8
(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 2 h / 0 °C

2: 890 mg / N-methylmorpholine; EDC; HOBT / CH₂Cl₂ / 20 °C

3: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

4: 362 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

5: 88 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

With 4-methyl-morpholine; pyridine; lithium hydroxide; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 4: Mitsunobu reaction;
DOI:10.1021/ja021327y

Reference yield:

: 519002-38-1
(R)-4-benzyl-3-((2R,3S,4S)-(E)-3-hydroxy-2,4-dimethyl-oct-6-enoyl)-oxazolidin-2-one

: (E)-(2R,3S,4S)-3-hydroxy-2,4-dimethyl-oct-6-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 2 h / 0 °C

2: 890 mg / N-methylmorpholine; EDC; HOBT / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; lithium hydroxide; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja021327y