Facile synthesis of 4-deoxy-4-fluoro-alpha-D-talopyranoside, 4-deoxy-4-fluoro-alpha-D-idopyranoside and 2,4-dideoxy-2,4-difluoro-alpha-D-talopyranoside

Journal article

The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-α- d-talopyranoside served as a precursor to 4-deoxy-4-fluoro-α-d- idopyranoside, allowing for inversion of configuration at C-3 via a three-step protocol. The synthesis of 2,4-dideoxy-2,4-difluoro-α-d-talopyranoside is based on two nucleophilic fluorination events at C-2 then at C-4 using TBAF·3H2O and TBAF·4tBuOH as a fluoride source. All compounds are prepared as pure stereoisomers and are therefore suitable probes for OH⋯F H-bonding studies by 1H NMR spectroscopy. © 2011 Elsevier B.V. All rights reserved.

Authors: Giuffredi, G; Jennings, L; Bernet, B; Gouverneur, V

• Publication status: Published
• Journal: JOURNAL OF FLUORINE CHEMISTRY
• Volume: 132
• Issue: 10
• Pages: 772-778
• Publication date: 2011-10-01
• DOI: 10.1016/j.jfluchem.2011.05.017
• ISSN: 0022-1139
• Language: English
• Keywords: alpha-D-Idopyranoside, 4-fluoro; alpha-D-Talopyranoside, 4-fluoro; Fluorinated carbohydrates; Tetrabutylammonium fluoride tetra-tert-butanol; alpha-D-Talopyranoside, 2,4-difluoro