Hirsch J, Koós M, Kovác P
Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovak Republic.
Carbohydr Res. 1998 Aug;310(1-2):145-9. doi: 10.1016/s0008-6215(98)00161-x.
Treatment of 1,3,4-tri-O-acetyl-alpha-D-xylopyranose with methyl 2,3-di-O-benzyl-l-chloro-l-deoxy-4-O-methyl-alpha, beta-D-glucopyranuronate in the presence of silver trifluoromethanesulfonate was highly stereoselective to give the alpha-linked aldobiouronic acid derivative (4) in 86% yield, after hydrogenolysis of the crude product of the coupling and chromatography. Compound 4 was acetylated and the fully protected substance was converted to the corresponding glycosyl chloride. Reaction of the latter with p-nitrophenol under phase-transfer catalysis afforded, after deacetylation, p-nitrophenyl 2-O-(methyl 4-O-methyl-alpha-D-glucopyranosyluronate)-beta-D-xylopyranoside.
在三氟甲磺酸银存在下，用2,3-二-O-苄基-l-氯-l-脱氧-4-O-甲基-α,β-D-吡喃葡萄糖醛酸甲酯处理1,3,4-三-O-乙酰基-α-D-吡喃木糖，具有高度立体选择性，在对粗偶联产物进行氢解和色谱分离后，以86%的产率得到α-连接的醛二糖醛酸衍生物(4)。化合物4被乙酰化，并且将完全保护的物质转化为相应的糖基氯。在相转移催化下，后者与对硝基苯酚反应，在脱乙酰化后得到对硝基苯基2-O-(甲基4-O-甲基-α-D-吡喃葡萄糖醛酸基)-β-D-吡喃木糖苷。
