benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate

Base Information

• Chemical Name: benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate
• CAS No.: 90472-77-8
• Molecular Formula: C₂₇H₂₆N₂O₆
• Molecular Weight: 474.513

Synonyms:benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate

Chemical Property of benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate

Chemical Property:

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Technology Process of benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate

There total 2 articles about benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate 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: 79.0%

benzyl D-2--phenylpropionate (90472-76-7) → benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate (90472-77-8)

Guidance literature:

With dimethyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 19 - 26 ℃;

DOI:10.1016/S0040-4020(01)91243-8

Reference yield:

N-benzyloxycarbonyl-serine 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester (59246-12-7) → benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate (90472-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / Et₃N / CH₂Cl₂ / 1.) -10 deg C, 30 min, 2.) up to rt

2: 79 percent / triphenyl phosphine, dimethyl azodicarboxilate / CH₂Cl₂ / 19 - 26 °C

With dimethyl azodicarboxylate; triethylamine; triphenylphosphine; In dichloromethane;

DOI:10.1016/S0040-4020(01)91243-8

Reference yield:

benzyl<1-<1(R)-(benzyloxycarbonyl)phenethyloxy>-2-oxo-3(S)-azetidinyl>-carbamate (90472-77-8) → 2(R)-<3(S)-amino-2-oxo-1-azetidinyloxy>-3-phenylpropionic acid (90472-89-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4.5h;

DOI:10.1016/S0040-4020(01)91243-8

upstream raw materials:

benzyl D-2--phenylpropionate

N-benzyloxycarbonyl-serine 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

Downstream raw materials:

2(R)-<3(S)-amino-2-oxo-1-azetidinyloxy>-3-phenylpropionic acid

2(R)-<1(S)-<2-(2-amino-4-thiazolyl)-2(Z)-(methoxyimino)-acetamido>-2-oxo-1-azetidinyloxy>-3-phenylpropionic acid

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