(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester

Base Information

• Chemical Name: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester
• CAS No.: 70579-79-2
• Molecular Formula: C₃₃H₃₇N₇O₉S₂
• Molecular Weight: 739.83
• Mol file: 70579-79-2.mol

Synonyms:

Chemical Property of (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester

There total 2 articles about (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl 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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester (70579-79-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: (i) NaI, acetone, (ii) /BRN= 5406309/, DMF

With triethylamine;

DOI:10.1021/jm00192a010

Reference yield:

L-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate (34573-39-2) + cefamandole (65338-32-1,144125-09-7,34444-01-4) → (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester (70579-79-2)

Guidance literature:

Multistep reaction; (i) NaI, acetone, (ii) /BRN= 5406309/, DMF;

DOI:10.1021/jm00192a010

Reference yield:

(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester (70579-79-2) → (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid L-phenylalanyloxy-methyl ester

Guidance literature:

With trifluoroacetic acid;

DOI:10.1021/jm00192a010

upstream raw materials:

L-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate

cefamandole

N-tert-butoxycarbonyl-L-phenylalanine