Synthesis of a selectively protected trisaccharide building block of the capsular polysaccharide of streptococcus pneumoniae types 6A and 6B

Ted M. Slaghek, Michiel J. van Vliet, Augustinus A.M. Maas, Johannis P. Kamerling, Johannes F.G. Vliegenthart*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

22 Citations (Scopus)

Abstract

4-Methoxybenzyl 2,4-di-O-benzyl-3-O-[2,4,6-tri-O-benzyl-3-O-(3,4,6-tri-O-benzyl-α-d-galactopyranosyl)-α-d- glucopyranosyl]-α-l-rhamnopyranoside (22), a building block for the α-d-Galp-(1→3)-α-d-Glcp-(1→3)-α-l-Rhap fragment of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B [→2)-α-d-Galp-(1→3)-α-d-Glcp-(1→3)-α-l- Rhap-(1→X)-d-RibOH-(5-Pn (6A, X = 3; 6B, X = 4) has been synthesised. Ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-d-glucopyranoside was coupled with 4-methoxybenzyl 2,4-di-O-benzyl-α-l-rhamnopyranoside in ether, using methyl triflate as promoter. The resulting α-d-Glcp-(1→3)-α-l-Rhap derivative was deallylated with KOBut in N,N-dimethylformamide followed by 0.1m HCl in 9:1 acetone-water. The product was coupled with 3,4,6-tri-O-acetyl-2-O-allyl-α,β-d-galactopyranosyl trichloroacetimidate in ether, using trimethylsilyl triflate, to yield 19. Deacetylation, benzylation, and deallylation then gave 22.

Original languageEnglish
Pages (from-to)75-86
Number of pages12
JournalCarbohydrate Research
Volume195
Issue number1
DOIs
Publication statusPublished - 21 Dec 1989
Externally publishedYes

Fingerprint Dive into the research topics of 'Synthesis of a selectively protected trisaccharide building block of the capsular polysaccharide of streptococcus pneumoniae types 6A and 6B'. Together they form a unique fingerprint.

Cite this