Wu X, Mariño-Albernas J R, Auzanneau F I, Verez-Bencomo V, Pinto B M
Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada.
Carbohydr Res. 1998 Feb;306(4):493-503. doi: 10.1016/s0008-6215(97)10101-x.
An improved synthesis of propyl 4-O-(3,6-di-O-methyl- beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L - rhamnopyranosyl]-3-O-methyl-alpha-L-rhamnopyranoside is also reported. The di- and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
描述了一种改进的合成方法，该方法使用三氯乙酰亚胺酯作为糖基供体，合成了丙基4-O-(3,6-二-O-甲基-β-D-吡喃葡萄糖基)-2,3-二-O-甲基-α-L-鼠李吡喃糖苷，这是一种与麻风分枝杆菌酚糖脂相对应的二糖。该合成策略还应用于制备三种含有13C标记甲基的相应二糖类似物。还报道了三糖丙基2-O-[4-O-(3,6-二-O-甲基-β-D-吡喃葡萄糖基)-2,3-二-O-甲基-α-L-鼠李吡喃糖基]-3-O-甲基-α-L-鼠李吡喃糖苷的制备。通过1H和13C NMR光谱对二糖和三糖进行了表征。
