Solid-phase synthesis of a branched hexasaccharide using a highly efficient synthetic strategy

被引：51

作者：

Roussel, F ^{[1
]}

Takhi, M ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 25期

关键词：

D O I：

10.1021/jo016018p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solid-phase synthesis of branched lacto-N-neohexaose derivative 1 occurring in human milk is described. The new building block of lactose 3 bearing the orthogonal temporary hydroxy protecting groups 9-fluorenylmethyloxycarbonyl (Fmoc) and levulinoyl (Lev) has been prepared. Its use, together with that of lactosamine donor 4, glucosamine donor 5, and O-galactosyl trichloroacetimidate 6, has enabled the preparation of hexasaccharide 22 following two different approaches in excellent overall yield (43%, 90% per step over eight steps). An additional key feature of this work is the successful use of newly prepared ester-type linker 2, having a benzylic spacer connected to the anomeric oxygen. This linker presents the advantage of producing a benzylic anomeric moiety after cleavage from the polymer support, which could be easily removed to obtain the unprotected oligosaccharide 1.

引用

页码：8540 / 8548

页数：9

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