Synthesis of two branched heptopyranoside‐ (L,D‐Hepp)‐containing trisaccharides of the inner‐core region of Citrobacter PCM 1487

G. J.P.H. Boons*, M. Overhand, G. A. van der Marel, J. H. van Boom

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The diastereogenic addition of (phenyldimethylsilyl)magnesium chloride to methyl 3‐O‐allyl‐2,4‐di‐O‐benzyl‐α‐D‐manno‐hexodialdo‐1,5‐pyranoside gave a L‐glycero‐D‐manno‐heptopyranoside (L,D‐Hepp) derivative having at C‐7 the phenyldimethylsilyl function as a hydroxy‐masking group. The L,D‐Hepp) derivative was converted into two acceptors which could be applied successfully for the preparation of the trisaccharides L‐α‐D‐Hepp)‐(1→3)‐O‐[L‐α‐D‐Hepp‐(1→7)]‐L‐α‐D‐Hepp/‐O‐Me 20 and α‐D‐Glcp‐(1→3)‐O‐[L‐α‐D‐Hepp‐(1→7)]‐L‐D‐Hepp‐O‐Me 26.

Original languageEnglish
Pages (from-to)144-148
Number of pages5
JournalRecueil des Travaux Chimiques des Pays‐Bas
Volume111
Issue number3
DOIs
Publication statusPublished - 1 Jan 1992
Externally publishedYes

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