Synthesis of sulfated alkyl malto and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection

Article abstract of DOI:10.1016/0008-6215(94)80021-9

A series of sulfated alkyl oligosaccharides, including a sulfated dodecyl laminarapentaoside and a sulfated octadecyl maltohexaoside with potent anti-human immunodeficiency virus (HIV) activity, has been synthesized.An alkyl oligosaccharide in which a long alkyl group is bonded to the reducing end of the oligosaccharide was first synthesized in high yield.Peracetylated oligosaccharides reacted with such aliphatic alcohols as 1-decyl and 1-dodecyl alcohols with Lewis acids as catalysts.As in the glycosylation of the α and β peracetylated glycosides, the β-anomer reacted exclusively, the acetylation was carried out with a sodium acetate-acetic anhydride at high temperatures to maximize the proportion of the β-anomer.