硫酸软骨素二糖重复片段的合成  

Synthesis of chondroitin sulfate disaccharide repeats

作　　者：王宏玲 罗盛 杨劲松[1] WANG Hongling;LUO Sheng;YANG Jinsong(West China School of Pharmacy,Sichuan University,Chengdu,Sichuan,610041P.R.China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《华西药学杂志》2022年第1期15-18,共4页West China Journal of Pharmaceutical Sciences

摘　　要：目的设计一种新的方法合成硫酸软骨素二糖骨架。方法以2位三氯乙氧羰基、4,6位苯亚甲基保护的氨基半乳糖苯硫苷为供体,以2位苯甲酰基、3位烯丙基、6位对溴苄基保护的对甲氧基苯基葡萄糖苷为受体,在NIS、TfOH催化下得到了二糖Ⅰ,并用^(1)HNMR、^(13)CNMR和^(1)H-^(1)HCOSY、HMBC、HMQC、HRMS(ESI)验证化合物的结构。结果在糖苷化步骤中,以82.9%的高收率得到了二糖Ⅰ。结论该二糖可作为不同类型硫酸软骨素合成的前体。OBJECTIVE To synthesize chondroitin sulfate disaccharides keleton.METHODS 2-trichloroethoxycarbonyl,4,6-benzenemethyl protected galactosamine phenylglucoside was used as donor,and 2-benzoyl,3-allyl and 6-bromobenzyl protected p-methoxyphenyl glucoside were used as receptors,finally achieving the synthesis of disaccharideⅠunder the catalysis of NIS and TfOH.The structure of the compound was verified by;HNMR,;CNMR,;H-;HCOSY,HMBC,HMQC and HRMS(ESI).RESULTS DisaccharideⅠwas obtained with a high yield of 82.9%in the glycosidation step.CONCLUSION The disaccharide can be used as a precursor for the synthesis of different types of chondroitin sulfate.

关 键 词：硫酸软骨素 二糖 二糖重复片段 寡糖合成 糖苷化反应 合成 立体选择性 正交保护 

分 类 号：R914[医药卫生—药物化学]