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Synlett 2000; 2000(1): 22-26
DOI: 10.1055/s-2000-6456
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Template Directed Cyclo-Glycosylation: A Convenient Approach to Unsymmetrical Isophthalic Disaccharide Esters. Influence of the Spacer in the Stereochemistry of the Glycosylation

Serafín Valverde* , Mercedes García, Ana M. Gómez, J. Cristóbal López
  • *Instituto de Química Orgánica General, C.S.I.C., Juan de la Cierva 3, Madrid 28006, Spain; Fax + 34 91 5 64 48 53; E-mail: iqov105@iqog.csic.es
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Publication Date:
31 December 2000 (online)

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When used in intramolecular glycosylation processes unsymmetrical isophthaloyl ester disaccharides display different stereochemical behaviour when compared to the corresponding phthaloyl ester disaccharides. The isophthaloyl ester disaccharides consist of a glycosyl donor and an acceptor, and are conveniently prepared by sequential coupling reactions of dialkylstannylene acetals derived from carbohydrates with 3-(2-mercapto-benzothiazolylcarbonyl)-benzoyl chloride.

intramolecular glycosylations - esterification - thiol esters - dialkylstannyl acetals - disaccharides

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