Wang Z G, Zhang X F, Ito Y, Nakahara Y, Ogawa T
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Bioorg Med Chem. 1996 Nov;4(11):1901-8. doi: 10.1016/s0968-0896(96)00172-1.
Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide 1a. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides.
制备了具有作为立体控制辅助基团的硫苯基和作为离去基团的硫甲基的唾液酸供体5，并将其用于模型糖基化反应。与受体底物6、7和8的反应分别以比先前观察到的溴化物1a更高的效率得到偶联产物9b、10b和11b。该反应进一步应用于受保护的糖氨基酸片段12的合成，该片段是为含唾液酸糖肽的合成而精心设计的。
