(6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 131614-17-0
• Molecular Formula: C₂₄H₂₄N₂O₇
• Molecular Weight: 452.464

Synonyms:(6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property:

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Technology Process of (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

There total 8 articles about (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 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: 77.0%

3-[(2R,3S)-3-Benzyloxycarbonylamino-1-(4-methoxy-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid phenyl ester (131614-15-8) → (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (131614-17-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97052-7

Reference yield: 76.0%

[(3S,4R)-3-Benzyloxycarbonylamino-2-oxo-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (131533-87-4) → (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (131614-17-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97052-7

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (6R,7S)-7-Benzyloxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (131614-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / THF

2: O₃ / methanol; CH₂Cl₂

3: DCC, DMAP / CH₂Cl₂

4: 76 percent / KOt-Bu / tetrahydrofuran / -78 °C

With dmap; potassium tert-butylate; sodium hydride; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)97052-7

upstream raw materials:

3-[(2R,3S)-3-Benzyloxycarbonylamino-1-(4-methoxy-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid phenyl ester

[(3S,4R)-3-Benzyloxycarbonylamino-2-oxo-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester

p-Methoxybenzyl bromide

(3S,4R)-3-amino-4-[2-(furan-2-yl)ethyl]azetidin-2-one

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