Constrained 3,6-anhydro-heptosides: Synthesis by a dast-induced debenzylative reaction, and reactivity profile

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Abstract

We report the first synthesis of a conformationally constrained 3,6-anhydroheptoside analogue of D-glycero-D-manno-heptopyranose 7-phosphate by a DAST (diethylaminosulfur trifluoride)-induced intramolecular cycloetherification. The reactivity of a series of constrained bicyclic 3,6-anhydro-thioheptosides as glycosyl donors was also studied in glycosylation reactions and compared with the reactivities of related unconstrained mannose and heptose scaffolds. Competition experiments confirmed that in the D-manno-heptose series, a reversal of chair conformation leads to an enhancement of the anomeric reactivity. A series of constrained bicyclic 3,6-anhydro-thioheptosides was prepared by regioselective cycloetherification, and their reactivities were compared to those of the corresponding heptosides.

Original languageEnglish
Pages (from-to)7593-7603
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number33
DOIs
Publication statusPublished - 1 Nov 2013

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Keywords

  • Carbohydrates
  • Conformation analysis
  • Cyclization
  • Glycosylation
  • Phosphorylation

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