Katsuraya K, Ikushima N, Takahashi N, Shoji T, Nakashima H, Yamamoto N, Yoshida T, Uryu T
Institute of Industrial Science, University of Tokyo, Japan.
Carbohydr Res. 1994 Jul 4;260(1):51-61. doi: 10.1016/0008-6215(94)80021-9.
A series of sulfated alkyl oligosaccharides, including a sulfate 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 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.
