88962-58-7

Basic information

• Product Name: N-Benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-seryl-L-leucin-2-chlorethylester
• CAS NO: 88962-58-7
• Molecular Weight: 745.178
• Mol File: 88962-58-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-Benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-seryl-L-leucin-2-chlorethylester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-seryl-L-leucin-2-chlorethylester(88962-58-7)
• EPA Substance Registry System: N-Benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-seryl-L-leucin-2-chlorethylester(88962-58-7)

Safety Data

• Hazardous Substances Data: 88962-58-7(Hazardous Substances Data)

Upstream product

• 20790-82-3 L-Leucine 2-chloroethyl ester hydrochloride 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 61-90-5 L-leucine 
• 88962-35-0 N-Benzyloxycarbonyl-L-seryl-L-leucin-2-chlorethylester 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 528-93-8 silver salicylate 

Relevant articles and documents

Glycopeptide Synthesis: Selective C-terminal Deblocking and Peptide Chain Elongation of Glucosylserine Derivatives

Benzyloxycarbonyl-(Z-)serine 2-bromoethyl ester (3b) reacts with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide (14) to give the glucosylserine ester 15.After conversion into the corresponding 2-iodoethyl ester 23 the carboxylic group is deblocked selectively by reductive elimination using zinc.In this procedure the Z and the carbohydrate protective functions as well as the sensitive O-glycoside bond remain unaffected.The glycosylserine 24 is condensed with amino acid 2-bromoethyl esters 2 to form protected glycodipeptide 2-bromoethyl esters 18 which are extended to give glycotripeptide esters 25 after selective carboxyl deblocking.Whereas protected serine dipeptides 5 are glycosylated with 14 to form the conjugates 18, the glycosylation of the serine tripeptides 10 was not successful.