環胺基酸酯結合非對稱胺基保護在寡糖合成上的應用

Abstract

本篇論文要報導芐基(benzyl group)取代的oxazolidinone和非對稱胺基保護(desymmetric amino protection)的應用性。我們應用此合成策略製備了一型和二型的乳糖胺，此方法不但容易操作而且有著極佳的產率。無論是在氮原子上面的芐氧羰(benzyloxycarbonyl group)和芐基，或是在氧原子上的芐基，都可以在溫和條件下的氫解反應(hydrogenolysis)中一併去除。接著我們合成出H型血基質(H blood group substrate)中的部分三醣結構，再度證明此一策略的應用性。

Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type 1 and type 2 LacNAc disaccharide in satisfactory yield. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. Further application of this protection strategy realizes the synthesis of trisaccharide H blood group substrate.