Elsevier

Tetrahedron

Volume 48, Issue 22, 1992, Pages 4649-4658
Tetrahedron

Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

https://doi.org/10.1016/S0040-4020(01)81239-4Get rights and content

Abstract

The disaccharide α-d-GlcNacp-(1-5)-β-KDO-2-OCH2CH2CH2NH2 containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-d-glucopyranoside. The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-d-mannitol.

A stereoselective route to the KDO-containing disaccharide II of the capsular polysaccharide I from Haemophilus (Actinobacillus) Pleuropneumoniae serotype 5 is reported.

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