Synthesis of 3-substituted xylopyranosides from 2,3-anhydropentosides

Fulgentius N. Lugemwa, Laura Denison

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Abstract

The facile regio- and stereoselective epoxide ring-opening of anhydropentosides described herein provides an attractive pathway to 3-substituted analogs of pentosides. Benzyl 2,3-anhydro-β-D-ribopyranoside (2) and benzyl 2,3-anhydro-β-L-ribopyranoside (7) were obtained from benzyl β-D-arabinopyranoside (1) and benzyl β-L-arabinopyranoside (3) respectively. The anhydropentosides were converted to the corresponding new 3-aminoderivatives (8, 9, 10, and 11), alkoxy derivatives (12, 13, and 14), and deoxy sugar (15) in high yield. Every conversion was a one-step reaction of the anhydroglycoside with the appropriate nucleophile. Side-products due to epoxide migration were not observed.

Original languageEnglish (US)
Pages (from-to)1433-1443
Number of pages11
JournalJournal of Carbohydrate Chemistry
Volume16
Issue number9
DOIs
Publication statusPublished - Jan 1 1997

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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