N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER

Base Information

• Chemical Name: N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER
• CAS No.: 64187-42-4
• Molecular Formula: C19H19 N O4
• Molecular Weight: 325.39
• Mol file: 64187-42-4.mol

Synonyms:N-Benzyloxycarbonyl-L-phenylalaninevinyl ester; N-Carbobenzoxy-L-phenylalanine vinyl ester; NSC 347521

Chemical Property of N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER

There total 2 articles about N-CARBOBENZOXY-L-PHENYLALANINE VINYL 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: 94.0%

N-Cbz-L-Phe (1161-13-3) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → N-benzyloxycarbonyl-L-phenylalanine vinyl ester (64187-42-4)

Guidance literature:

With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine; In tetrahydrofuran; at 50 ℃; for 16h;

DOI:10.1002/adsc.201800914

Reference yield: 60.0%

vinyl acetate (108-05-4,9003-20-7) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-L-phenylalanine vinyl ester (64187-42-4)

Guidance literature:

L-phenylalanine; benzyl chloroformate; With sodium hydroxide; In water; toluene; at 0 ℃; for 16h;

vinyl acetate; With palladium diacetate; potassium hydroxide; at 20 ℃; Further stages.;

DOI:10.1039/b104137c

Reference yield: 60.0%

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) + N-benzyloxycarbonyl-L-phenylalanine vinyl ester (64187-42-4) → methyl 6-O-carboxyl-(N-benzyloxycarbonyl-L-phenylalanine)-α-D-mannopyranoside

Guidance literature:

With pyridine; subtilisin Bacillus lentus (EC 3.4.21.14); at 45 ℃; for 500h;

DOI:10.1039/b104137c

upstream raw materials:

vinyl acetate

L-phenylalanine

benzyl chloroformate

N-Cbz-L-Phe

Refernces

• 1、 Boyer,Stanchev,Fairbanks,Davis. "Ready protease-catalyzed synthesis of carbohydrate-amino acid conjugates.". . p. 1908 - 1909. Retrieved 2007/10/03.