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

✍ Scribed by G. J. P. H. Boons; M. Overhand; G. A. van der Marel; J. H. van Boom

• Book ID: 104589398
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 563 KB
• Volume: 111
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19921110306

✦ Synopsis

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‐Hep__p__) derivative having at C‐7 the phenyldimethylsilyl function as a hydroxy‐masking group. The L,D‐Hep__p__) derivative was converted into two acceptors which could be applied successfully for the preparation of the trisaccharides L‐α‐D‐Hep__p__)‐(1→3)‐O‐[L‐α‐D‐Hepp‐(1→7)]‐L‐α‐D‐Hep__p__/‐O‐Me 20 and α‐D‐Glc__p__‐(1→3)‐O‐[L‐α‐D‐Hep__p__‐(1→7)]‐L‐D‐Hep__p__‐O‐Me 26.