β-D-甘露糖醛酸二糖片段的合成  

Synthesis of β-D-mannuronic acid disaccharide fragments

作　　者：陈朋伟 张永振[1] 杨中舟 王鹏[1] 李明[1] 

机构地区：[1]中国海洋大学海洋药物教育部重点实验室医药学院,山东青岛266003

出　　处：《中国海洋药物》2014年第2期63-68,共6页Chinese Journal of Marine Drugs

基　　金：国家自然科学基金项目(21272220);山东省科技发展计划(2012GHY11526);海洋公益性行业科研专项经费(201005024);长江学者和创新团队发展计划项目(IRT0944)资助

摘　　要：目的利用化学方法立体选择性地合成β-D-甘露糖醛酸二糖片段。方法以4,6位苄叉保护的甘露糖硫苷为原料合成亚砜苷供体10,再用Tf2O作为促进剂,亚砜苷供体10与2-三甲基硅基乙醇以及低活性的糖醛酸受体13进行糖苷化反应合成β-D-甘露糖醛酸单糖12和二糖14。结果糖苷化反应分别以72%和73%的产率,高立体选择性(β/α>20/1)得到β-D-甘露糖醛酸单糖12和二糖14,为β-D-甘露糖醛酸寡糖的合成提供物质基础和技术保障。Objective Stereoselective Chemical synthesis of β-D-mannuronic acid disaccharide fragments. Methods Phenyl α-D-mannopyranosyluronic acid methyl ester S-Oxide donor 10 was synthesized from Phenyl 4,6-O-benzylidene-l-thio-α-D-mannopyranoside 3. Using Tf20 as an activator, glycosylation of 10 with 2-trimethylsilyl ethanol and 13 gave β-D-mannuronic acid monosaccharide 12 and disaccharide 14. Results ffD-mannuronic acid monosaccharide 12 and disaccharide 14 were obtained in 72% and 73 % yields with high stereoselcctivity （β/α〉lO/1）, which were valuable for the synthesis of β-D-mannuron-ic acid oligosaccharides.

关 键 词：β-D-甘露糖醛酸 亚砜苷 糖苷化 寡糖合成 

分 类 号：R914[医药卫生—药物化学]