Synthesis of bis-(methyl 3,4,6-tri-O-acetyl-D-glucopyranosid-2-yl)-oxamides

The synthesis of a new bis-(D-glucopyranosid-2-yl)oxamides via the key intermediate, N-acetyl N-(methyl 3,4,6-tri-O-acetyl-α-D-glucopyranosid-2-yl) oxamic acid chloride (2α) is described. Treatment of compound 2α with methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside afforded N-(methyl 3,4,6-tri-O-acetyl-α-D-glucopyranosid-2-yl)-N′-(methyl 3,4,6-tri-O-acetyl-β-D-glucopyranosid-2-yl)-oxamide. Reaction of 2α with 1,2-diaminoethane afforded 1,2-bis-[N,N′-(methyl 3′,4′,6′-tri-O-acetyl-α-D-glucopyranosid-2′-yl)]ethyloxamide as a main product, while 2-N-[N′-(methyl 3′,4′,6′-tri-O-acetyl-α-D-glucopyranosid-2′-yl)oxamide]-ethyl acetamide was formed as a side product. Reaction of 2α with 1,3-diamino-2-hydroxypropane gave only 1,3-bis-N,N-[N′-(methyl 3′,4′,6′-tri-O-acetyl-2′-deoxy-α-D-glucopyranosid-2′-yl)-oxamido]-2-propanol.