化学
碘脲酸
双糖
糖醛酸
糖基供体
硫酸化
立体化学
肝素
酰胺
糖苷
葡萄糖醛酸
组合化学
有机化学
生物化学
多糖
作者
Supriya Dey,H. Christine Lo,Chi‐Huey Wong
摘要
Idraparinux is a fully O-sulfated α-methyl glycoside of heparin pentasaccharide motif known to interact with the antithrombin III domain and act as anticoagulant. The current most effective synthesis of Idraparinux is complicated and nonstereoselective, requiring numerous stepwise procedures with low yields. We report here an efficient modular one-pot synthesis of Idraparinux involving the use of a glycosyl phosphate with 6-O-tert-butyl diphenyl silyl group and a d-glucuronic acid-containing disaccharide thioglycoside with 6-O-acetyl group as donor building blocks for the α-directing one-pot glycosylations with an l-iduronic acid-containing disaccharide acceptor building block. The uronic acid was incorporated in a disaccharide module used in the one-pot synthesis to avoid the complicated late-stage installation of these acidic sugars. The one-pot synthesis of Idraparinux demonstrated here is an effective strategy and should be applicable to the modular assembly of other heparan sulfates with regiodefined sulfation pattern for functional study.
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