Synthesis of glycosyl diethylamino and piperidylcarbodithiolates

Abstract

Reaction of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-Dglucopyranosyl chloride (5) and 4-O-(2,3,4,6-tetra-O-acetyl-β–Dgalactopyranosyl)- D-2,3,4,6-tetra-O-acetyl-α-1-bromo-Dglucopyranoside (8) with sodium  diethylaminocarbodithiolate (3) or sodium pipe r idyl c a rbodi thiol a t e (4 ) ga ve the cor r e sponding glycosylcarbodithiolates, 2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β-D-glucopyranosyl 1- diethylaminocarbodithiolate (6) , 2-Acetamido-3,4,6-tri-O-acetyl-2- deoxy-β-D-glucopyranosyl 1-piperidylcarbodithiolate, (7), 4-O- (2,3,4,6-tetra-O-ac etyl -b-D-galac topyranosyl)-2,3,6- t r i-O-ac etyl -b-D-glucopyranosyl 1-  diethylaminocarbodithiolate (9) and 4-O-(2,3,4,6- tetra-O-ac etyl -b-D-galactopyranosyl) 2,3,6-tri-O-acetyl-b-Dglucopyranosyl 1-  piperridylcarbodithiolate (10) in good yield. The structures were confirmed by using elemental analysis, IR, 1H, 13C, and 2D NMR spectra.