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Synthesis 1989; 1989(10): 755-758
DOI: 10.1055/s-1989-27384
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A Convenient Synthesis of S-(α-D- and S-(β-D)-Glucopyranosyl-6-thiomaltodextrins

Sylvain Cottaz* , Hugues Driguez
  • *Centre de Recherches sur les Macromolécules Végétales, CNRS, B.P. 53X, F-38041 Grenoble cedex, France
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Publication Date:
02 May 2002 (online)

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(2,3-Di-O-acetyl-6-deoxy-6-iodo)-hexakis(2,3,6-tri-O-acetyl) cyclomaltoheptaose (9) was prepared by reaction of cyclomaltoheptaose (5) with trityl chloride followed by acetylation, O-detritylation, mesylation, and displacement of the mesyloxy group by iodine using sodium iodide. This cyclomaltoheptaose derivative was S-glycosylated in high yield with either of the anomers of 2,3,4,6-tetra-O-acetyl-S-acetyl-1-thioglucopyranose (1α or 1β). Deacetylation afforded S-(α -D- and S-(α-D-glucopyranosyl)-6-thiocyclomaltoheptaose (10b) and 11b, respectively. Procedures arising from model experiments also provided a new syntheses of S-(α-D-glucopyranosyl)-6-thiomaltose (3b) and of its β-isomer (4b).

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