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

✍ Scribed by Kaname Katsuraya; Naoya Ikushima; Nahoko Takahashi; Tadao Shoji; Hideki Nakashima; Naoki Yamamoto; Takashi Yoshida; Toshiyuki Uryu

• Book ID: 102996354
• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 775 KB
• Volume: 260
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)80021-9

✦ Synopsis

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 a and /3 peracetylated glycosides, the j3 anomer reacted exclusively, the acetylation was carried out with a sodium acetate-acetic anhydride at high temperatures to maximize the proportion of the /3 anomer.