SYNTHESIS OF SULFATED ALKYL MALTOSACCHARIDES AND LAMINARA-OLIGOSACCHARIDES WITH POTENT INHIBITORY EFFECTS ON AIDS VIRUS-INFECTION

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 l-decyl and l-dodecyl alcohols with Lewis acids as catalysts. As in the glycosylation of the alpha and beta peracetylated glycosides, the beta anomer reacted exclusively, the acetylation was carried out with a sodium acetate-acetic anhydride at high temperatures to maximize the proportion of the beta anomer.