A PRACTICAL SYNTHESIS OF MANNOSAMINYL-BETA(1-]4)-GLUCOSYL-ALPHA(1-]2)-RHAMNOSE THE TRISACCHARIDE REPEATING UNIT OF A STREPTOCOCCUS-PNEUMONIAE CAPSULAR POLYSACCHARIDE

被引：34

作者：

KAJI, E ^{[1
]}

LICHTENTHALER, FW ^{[1
]}

OSA, Y ^{[1
]}

TAKAHASHI, K ^{[1
]}

ZEN, S ^{[1
]}

机构：

[1] TH DARMSTADT, INST ORGAN CHEM, D-64287 DARMSTADT, GERMANY

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 08期

关键词：

D O I：

10.1246/bcsj.68.2401

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient chemical synthesis is described for the title trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae Type 19F. The key intermediate was a well-accessible indirect beta-D-mannosaminyl donor, i.e. 2-(benzoyloxyimino)-2-deoxy-alpha-D-arabino-hexopyranosyl bromide, which underwent glycosidations with 20:1 beta-selectivities; the benzoyloxyimino group was reduced with essential manno specificity. The ManNAc-beta(1-->4)-Glc disaccharide, thus obtained in suitably blocked form, was subsequently converted into 1-fluoride, with which a L-rhamnosyl acceptor was glycosylated by an alpha(1-->2) linkage to yield the target trisaccharide in an altogether 6% overall yield for the 13 steps required from D-glucose.

引用

页码：2401 / 2408

页数：8

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