摘要
目的利用化学方法高效合成PI-88糖基片段a-(1→2)-甘露糖三糖。方法以4,6位苯亚甲基保护的D-甘露糖硫苷3为原料合成N-对甲苯磺酰亚胺酯供体6,以TMSOTf作为促进剂,供体6与受体3进行糖苷化反应,得到a-(1→2)甘露糖二糖7,然后将二糖脱除苯甲酰基,再次与供体6进行糖苷化反应,合成出糖基片段a-(1→2)甘露糖三糖2。结果以85%和79%的糖苷化反应产率,得到a-(1→2)甘露糖二糖7和三糖2,为PI-88构效关系的研究提供物质基础和保障。
Objective An efficient synthesis of a-（1→2）-mannotrisacchride was achieved.The target was designed to mimic the promising anticancer agent PI-88.Method The glycosyl N-tosyl benzimidate 6was prepared from phenyl 4,6-O-benzylidene-3-O-（2-naphthylmethyl）-1-thio-a-D-mannopyranoside 3.The analogue 7was obtained from the glycosyl N-tosyl benzimidate 6with acceptor 8in the presence of TMSOTf at 0 ℃ and removal of benzoyl groups in 7to obtain acceptor 8,then 8reacted with 6to give trisaccharide 2.Results The desired mannose disacchride 7and trisaccharide 2were obtained in 85%and79% glycosidic yield,which was valuable for studying the structure and activity relationship of PI-88.
出处
《中国海洋药物》
CAS
CSCD
2015年第6期69-74,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项目(2012GHY11526)资助
