118358-94-4

Upstream product

• 118358-66-0 N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 

Downstream Products

• 105678-34-0 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-seryl-glycyl-L-isoleucyl-glycinbenzylester 
• 105678-35-1 3-O-(β-D-Xylopyranosyl)-L-seryl-glycyl-L-isoleucyl-glycin 

Relevant academic research and scientific papers

Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids

A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr 3 promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

SYNTHESE EINES XYLOSE-HALTIGEN GLYCOPEPTIDES, DAS DIE AMINOSAEURE-SEQUENZ 4 BIS 7 DES NH2-TERMINUS DER PROTEIN-CORE-STRUCTUR DES RINDERHAUT-PROTODERMATAN-SULFATS ENTHAELT

The synthesis is described of α-β-D-xylopyranosyl-L-serylglycyl-L-isoleucyl-glycine (7), a glycopeptide containing the amino acid sequence of the protein core-structure of beef-skin protodermatan sulfate; coupling of N-protected O-XylpSer with protected GlyIleuGly followed by deprotection afforded 7.