Johnston B D, Pinto B M
Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada.
Carbohydr Res. 1999 Feb 28;315(3-4):356-60. doi: 10.1016/s0008-6215(99)00024-5.
The use of acetylated phenyl 1-seleno-beta-D-galactofuranoside as a glycosyl donor for the synthesis of protected D-Galf-beta-(1-->3)-alpha-D-Manp as its methyl or ethylthio glycoside has been demonstrated. Activation of the selenoglycoside over a thioglycoside acceptor by NIS/TfOH is extremely selective and gives the ethylthio disaccharide in 91% yield. The parent disaccharide is found as a terminal and branched unit in the lipopeptidophosphoglycan oligosaccharides of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease.
已证明将乙酰化苯基 1-硒代-β-D-呋喃半乳糖苷用作糖基供体，用于合成其甲基或乙硫基糖苷形式的受保护 D-Galf-β-(1→3)-α-D-Manp。通过 NIS/TfOH 使硒代糖苷在硫代糖苷受体上活化具有极高的选择性，可得到产率为 91%的乙硫基二糖。母体二糖是原生动物克氏锥虫（恰加斯病的病原体）的脂肽磷糖寡糖中的末端和分支单元。
