Oscarson S, Svahnberg P
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Carbohydr Res. 1998 Jun;309(2):207-12. doi: 10.1016/s0008-6215(98)00107-4.
The synthesis of a the 2,4,3'-trideoxy and 2,4,3',4'-tetradeoxy analogues of the trimannoside part of the core structure of N-linked glycoproteins, methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside, is described. A 2,4-dideoxy (1-->6) linked disaccharide was used as a common intermediate acceptor, which was coupled with a 3-deoxy and a 3,4-dideoxy benzochlorosugar donor, the latter prepared from methyl alpha-D-mannopyranoside in five steps. Despite the acid-sensitive donors and acceptor, acceptable glycosylation yields were obtained of both the trideoxy- and the tetradeoxy trisaccharide using silver triflate as a promoter (65 and 51%, respectively). Deprotection in one step then gave the target products.
描述了N-连接糖蛋白核心结构的三甘露糖苷部分的2,4,3'-三脱氧和2,4,3',4'-四脱氧类似物，即3,6-二-O-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷甲酯的合成。一种2,4-二脱氧(1→6)连接的二糖被用作通用的中间体受体，其与3-脱氧和3,4-二脱氧苯并氯代糖供体偶联，后者由α-D-甘露吡喃糖苷甲酯经五步制备。尽管供体和受体对酸敏感，但使用三氟甲磺酸银作为促进剂时，三脱氧和四脱氧三糖均获得了可接受的糖基化产率（分别为65%和51%）。然后一步脱保护得到目标产物。
