M. Spinola, R. Jeanloz
Dec 1, 1970
Citations
0
Influential Citations
27
Citations
Journal
Carbohydrate Research
Abstract
Abstract Three asparagine derivatives serving as intermediates in the synthesis of glycopeptides have been synthesized. 2,3,6-Tri-O-acetyl-N-[1-benzyl N-(benzyloxy-carbonyl)- L -aspart-4-oyl]-4-O-(2,3,4,6-tetra-O-acetyl-β- D -galactopyranosyl)-β- D -glucopyranosylamine and the 2-acetamido-2-deoxy-β- D -glucopyranosylamine analog were respectively obtained from the fully acetylated lactose and lactosamine (2-amino-2-deoxy-4-O-β- D -galactopyranosyl- D -glucose) via the halides, azide, and amine, followed by condensation with 1-benzyl N-(benzyloxycarbonyl)- L -aspartate. 2-Acetamido-2-deoxy-β- D -glucopyranosyl azide was tritylated at O-6, the product was fully acetylated, the azide was reduced to the amine, and this was condensed with 1-benzyl N-(benzyloxycarbonyl)- L -aspartate; the resulting asparagine derivative was detritylated, and the product was condensed with 2,3,4,6-tetra-O-acetyl-α- D -galactopyranosyl bromide, to give 2-acetamido-N-[1-benzyl N-(benzyloxy-carbonyl)- L -aspart-4-oyl]-2-deoxy-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β- D -galactopyranosyl)-β- D -glucopyranosylamine.