(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

Chemical Name:(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone
CAS No.:110905-26-5
Molecular Formula:C₁₆H₁₈N₄O₄
Molecular Weight:330.343
Hs Code.:

Synonyms:(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

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Chemical Property of (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

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Technology Process of (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

There total 3 articles about (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone 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: 82.0%

: 110905-25-4
(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

: (R)-4-Benzyl-3-((S)-3-hydroxy-2-imino-4-methyl-pent-4-enoyl)-oxazolidin-2-one

: 110905-26-5
(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Guidance literature:: With sodium azide; In dimethyl sulfoxide; for 5h; Yields of byproduct given; Ambient temperature;
DOI:10.1021/ja00257a041

Reference yield:

: 40217-17-2,90719-32-7,120574-96-1,102029-44-7
(R)-4-(phenylmethyl)-2-oxazolidinone

: 110905-26-5
(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C

2: 1.) triethylamine, di-n-butylboryl triflate / 1.) diethyl ether, room temperature, 1.5 h, 2.) diethyl ether, -78 deg C, 30 min, 0 deg C, 2 h

3: 82 percent / sodium azide / dimethylsulfoxide / 5 h / Ambient temperature

With n-butyllithium; sodium azide; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1021/ja00257a041

Reference yield:

: 110905-24-3
(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

: 110905-26-5
(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) triethylamine, di-n-butylboryl triflate / 1.) diethyl ether, room temperature, 1.5 h, 2.) diethyl ether, -78 deg C, 30 min, 0 deg C, 2 h

2: 82 percent / sodium azide / dimethylsulfoxide / 5 h / Ambient temperature

With sodium azide; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dimethyl sulfoxide;
DOI:10.1021/ja00257a041