Zeng Youlin, Zhang Jianjun, Ning Jun, Kong Fanzuo
Research Center for Eco-Environmental Sciences, Academia Sinica, P.O. Box 2871, Beijing 100085, China.
Carbohydr Res. 2003 Jan 2;338(1):5-9. doi: 10.1016/s0008-6215(02)00402-0.
A mannose heptasaccharide existing in baker's yeast, Saccharomyces cerevisiae X2180-1A wild-type strain, was effectively synthesized as its allyl glycoside via TMSOTf-promoted condensation of a disaccharide donor 13 with a pentasaccharide acceptor 12, followed by deprotection. The pentasaccharide 12 was constructed by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9) with allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside (10), followed by deacetylation. The tetrasaccharide 9 was obtained by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (5) with allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (6), followed by deallylation and trichloroacetimidation. The disaccharides 6 and 13 were readily obtained by known methods.
存在于面包酵母酿酒酵母X2180 - 1A野生型菌株中的一种甘露庚糖，通过三甲基甲磺酸钪促进二糖供体13与五糖受体12缩合，随后脱保护，有效地合成了其烯丙基糖苷。五糖12是通过将2,3,4,6 - 四 - O - 苯甲酰基 - α - D - 甘露吡喃糖基 - (1→3) - 2,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖基 - (1→2) - 3,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖基 - (1→2) - 3,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖基三氯乙酰亚胺酯（9）与烯丙基6 - O - 乙酰基 - 3,4 - 二 - O - 苯甲酰基 - α - D - 甘露吡喃糖苷（10）偶联，随后脱乙酰化得到的。四糖9是通过将2,3,4,6 - 四 - O - 苯甲酰基 - α - D - 甘露吡喃糖基 - (1→3) - 2,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖基三氯乙酰亚胺酯（5）与烯丙基3,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖基 - (1→2) - 3,4,6 - 三 - O - 苯甲酰基 - α - D - 甘露吡喃糖苷（6）偶联，随后脱烯丙基化和三氯乙酰亚胺化得到的。二糖6和13可通过已知方法轻松获得。
