(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

Base Information

Chemical Name:(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one
CAS No.:489469-33-2
Molecular Formula:C₁₄H₁₇NO₅
Molecular Weight:280.285
Hs Code.:

Synonyms:(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

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Chemical Property of (4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

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Technology Process of (4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

There total 4 articles about (4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-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: 19.0%

: 489469-31-0
(4S)-3-(benzyloxycarbonyl)-4-(3-deuterioformylethyl)-1,3-oxazolidin-5-one

: 489469-33-2
(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

Guidance literature:: With S-alpine borane; In tetrahydrofuran; at 20 ℃; for 10h;
DOI:10.1021/jo026479q

Reference yield:

: 1155-62-0
N-benzyloxycarbonyl-L-glutamic acid

: 489469-33-2
(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / p-toluenesulfonic acid / toluene / 1.67 h / Heating

2: 100 percent / oxalyl chloride; DMF / CH₂Cl₂ / 0.5 h / 20 °C

3: 48 percent / D₂; lutidine / 5percent Pd/BaSO₄ / tetrahydrofuran / 2 h / 20 °C

4: 19 percent / (S)-Alpine borane / tetrahydrofuran / 10 h / 20 °C

With oxalyl dichloride; (S)-alpine borane; lutidine; toluene-4-sulfonic acid; N,N-dimethyl-formamide; deuterium; 5percent Pd/BaSO₄; In tetrahydrofuran; dichloromethane; toluene; 3: Rosenmund reduction / 4: Midland reduction;
DOI:10.1021/jo026479q

Reference yield:

: 58456-26-1
(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

: 489469-33-2
(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: 48 percent / D₂; lutidine / 5percent Pd/BaSO₄ / tetrahydrofuran / 2 h / 20 °C

2: 19 percent / (S)-Alpine borane / tetrahydrofuran / 10 h / 20 °C

With S-alpine borane; lutidine; deuterium; 5percent Pd/BaSO₄; In tetrahydrofuran; 1: Rosenmund reduction / 2: Midland reduction;
DOI:10.1021/jo026479q