methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate

Base Information

• Chemical Name: methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate
• CAS No.: 136642-82-5
• Molecular Formula: C₁₆H₁₉NO₆
• Molecular Weight: 321.33

Synonyms:methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate

Chemical Property of methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate

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Technology Process of methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate

There total 13 articles about methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (4S,5R)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid methyl ester (141394-65-2) → methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate (136642-82-5)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo061159i

Reference yield: 50.0%

methyl (S)-2-[bis(tert-butoxycarbonyl) amino]-3-phenylpropanoate (154409-62-8) → methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate (136642-82-5)

Guidance literature:

methyl (S)-2-[bis(tert-butoxycarbonyl) amino]-3-phenylpropanoate; With N-Bromosuccinimide; In tetrachloromethane; at 80 ℃; for 1h; Irradiation;

With silver nitrate; In acetone; at 20 ℃; for 16h; Darkness;

DOI:10.1021/acs.orglett.7b03967

Reference yield: 45.0%

β-bromo-N,N-bis(tert-butoxycarbonyl)-L-phenylalanine methyl ester → threo-β-bromo-N,N-bis(tert-butoxycarbonyl)-L-phenylalanine methyl ester + methyl (4S,5R)-3-N-tert-butoxycarbonyl-5-phenyl-1,3-oxazolidin-2-oxo-4-carboxylate (136642-82-5)

Guidance literature:

With silver carbonate; In acetone; at 20 ℃; for 2h;

DOI:10.1021/jo061159i

upstream raw materials:

(4S,5R)-5-Phenyl-2-thioxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester

di-tert-butyl dicarbonate

(4S,5R)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid methyl ester

benzaldehyde

Downstream raw materials:

methyl 2-(tert-butoxycarbonylamino)-3-phenylacrylate

erythro-N-(tert-butoxycarbonyl)-β-hydroxy-L-phenylalanine methyl ester

(2S,3S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-methoxybenzyloxy)-3-phenylpropanoate

tert-butyl (2S,3S)-1-(amino)-3-(4-methoxybenzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamate

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