85917-85-7

Upstream product

• 4779-31-1 Z-Asp-OBn 
• 85917-83-5 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranose 
• 204579-03-3 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 134003-35-3 pent-4-enyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 20379-61-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 85917-82-4 1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 20379-60-6 α-D-Glucopyranosyl azide 
• 136755-16-3 N-acetyl-2,3,4,6-tetra-O-benzyl-N-(benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine 

Relevant academic research and scientific papers

Neighbouring group participation of C-6 substituents of glucose derivatives on the stereoselectivity of the N-glycosidic linkage of glycopeptides

The first example of a glycopeptide with a direct N-α-glycosidic linkage between the trisaccharide and the amino acid residue was found in the glomerular basement membrane of rats. In connection with the total synthesis of nephritogenoside, glycosyl azides with different protecting groups and carbohydrate chain lengths are synthesized, reduced to the corresponding glycosyl amines and coupled with Z-Asp-OBzl. Remarkable differences in the α:β ratio of the condensation products are observed, caused by neighbouring group participation.

Application of n-pentenyl glycosides in the regio- and stereo-controlled synthesis of α-linked N-glycopeptides

The N-glycopeptides α-Glc-(1→Asn and α-Glc-(1→6)-β-Glc-(1→6)-α-Glc-(1→Asn have been synthesized efficiently from pent-4-enyl D-glucopyranoside derivatives. The methodology illustrates (a) a novel route for formation of the N-α-D-glucosyl-asparagine link,