Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-D-mannopyranosyl Uronates

被引：32
|
作者：
Walvoort, Marthe T. C. [1 ]
Moggre, Gert-Jan [1 ]
Lodder, Gerrit [1 ]
Overkleeft, Herman S. [1 ]
Codee, Jeroen D. C. [1 ]
van der Marel, Gijsbert A. [1 ]
机构：
[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 18期
关键词：
4,6-O-BENZYLIDENE-DIRECTED BETA-MANNOPYRANOSYLATION; CONTAINING GLYCAN CHAIN; STEREOCONTROLLED SYNTHESIS; TRIFLUOROMETHANESULFONIC ANHYDRIDE; PROTECTING GROUP; ACID; GLYCOSYLATION; SUBSTITUENT; GLYCOSIDES; DONORS;
D O I：
10.1021/jo201179p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly a-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.
引用
收藏
页码：7301 / 7315
页数：15
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