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Synthesis 2002(3): 0418-0426
DOI: 10.1055/s-2002-20038
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Short Route to Malto-trisaccharide Synthons: Synthesis of the Branched Nonasaccharide, 6′′′-α-Maltotriosyl-maltohexaose

Iben Damagera,c, Carl Erik Olsenb,c, Birger Lindberg Møllera,c, Mohammed Saddik Motawia*a,c
a Carbohydrate Chemistry Group at Plant Biochemistry Laboratory, Department of Plant Biology, The Royal Veterinary and Agricultural University, 40 Thorvaldsensvej, 1871 Frederiksberg C, Copenhagen, Denmark
b Department of Chemistry, The Royal Veterinary and Agricultural University, 40 Thorvaldsensvej, 1871 Frederiksberg C, Copenhagen, Denmark
c Center for Molecular Plant Physiology (PlaCe), The Royal Veterinary and Agricultural University, 40 Thorvaldsensvej, 1871 Frederiksberg C, Copenhagen, Denmark
Fax: +4535283333; e-Mail: mosm@kvl.dk;
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Publication History

Received 8 October 2001
Publication Date:
28 July 2004 (online)

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Abstract

A short route to phenyl 1-thio-β-maltotrioside derived building blocks and their use for the synthesis of the branched nona­saccharide, 6′′′-α-maltotriosyl-maltohexaose, is described. Instead of using glucose and maltose as starting materials, maltotriose was used and synthetically manipulated in a well designed strategy to obtain phenyl O-(2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl)-(1→4)-O-(2,3,6-tri-O-benzyl-α-d-glucopyranosyl)-(1→4)-2,3-di-O-benzyl-1-thio-β-d-glucopyranoside, phenyl O-(2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl)-(1→4)-O-(2,3,6-tri-O-benzyl-α-d-glucopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-1-thio-β-d-glucopyranoside and phenyl O-(2,3,6-tri-O-benzyl-α-d-glucopyranosyl)-(1→4)-O-(2,3,6-tri-O-benzyl-α-d-glucopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-1-thio-β-d-glucopyranoside. The described methodology has shortened multi-step synthesis of the desired branched nonasaccharide from 40 to 23 steps. It has also provided maltotriose derived building blocks that independently or in combination with corresponding glucose or maltose derived building blocks permit synthesis of any desired part of the amylopectin or amylose molecule.

Key words

1,3-benzodithiolan-2-ylium protecting group - carbohydrates - glycosides - 6′′′-α-maltotriosyl-maltohexaose - phase transfer catalysis