Nilsson M, Svahn C M, Westman J
Organic Chemistry, Kabi Pharmacia AB, Stockholm, Sweden.
Carbohydr Res. 1993 Aug 17;246:161-72. doi: 10.1016/0008-6215(93)84030-a.
The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2-deoxy-alpha-D- glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-beta-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2- deoxy-alpha-D-glucopyranosyl)-(1-->4)-O-beta-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.
从肝素中分离得到的一种四糖的甲基糖苷、O-(α-L-艾杜吡喃糖醛酸)-(1→4)-O-(2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基)-(1→4)-O-(β-D-吡喃葡萄糖醛酸)-(1→3)-O-β-D-吡喃半乳糖苷二钠盐及其三糖衍生物、O-(α-L-艾杜吡喃糖醛酸)-(1→4)-O-(2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基)-(1→4)-O-β-D-吡喃葡萄糖醛酸二钠盐，采用逐步合成法合成。一种合适的艾杜糖醛酸和葡糖胺（艾杜糖醛酸-葡糖胺）的保护二糖片段用作合成的关键中间体，并分别与一种保护的半乳糖衍生物和一种葡糖醛酸和半乳糖（葡糖醛酸-半乳糖）的二糖片段进行糖苷化反应，得到三糖和四糖衍生物。脱保护得到目标化合物。
