SYNTHESES OF D-GLUCOSAMINYL BOLAAMPHIPHILES

Twelve N-acetyl or NH2-free D-glucosaminyl bolaamphiphiles have been s ynthesized by the intermediate of N-allyloxycarbonyl-D-glucosaminyl pr ecursors. Thus, glycosylation of alpha,omega-diols with yl-2-allyloxyc arbonyl-2-deoxy-beta-D-glucopyranose (1) gave the bis(glycosides) 2a-h in good yields and without column chromatography. Alkaline treatment of these derivatives followed by acetylation gave the peracetylated N- acetyl compounds 3a-h which were further deprotected by the Zemplen de acetylation procedure to the N-acetyl-D-glucosaminyl boiaamphiphiles 4 a-h. The bis(glycosides) 2c,d,g were also transformed into the O-acety lated amino-free derivatives Sc,d,g by chemospecific deprotection of t he N-allyloxycarbonyl groups with palladium (0). Further deprotection of the ester functions led to the completely deprotected bolaamphiphil es 7c,d,g with high yields. Fully deprotected compounds 7a,d,g,h were also obtained from 2a,d,g,h by alkaline treatment and purification by column chromatography. Surface tension measurements were realized for aqueous solutions containing the soluble bolaamphiphiles.