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
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...
| Main Authors: | , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2011
|
| Summary: | 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. |
|---|