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Caravano, Audrey, Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275, Percy, Jonathan M., Rinaudo, Giuseppe, Roig, Ricard and Singh, Kuldip
(2009)
Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses.
Organic and Biomolecular Chemistry, 7 (5).
pp. 996-1008.
ISSN 1477-0520
Abstract
Free radical bromination and nucleophilic fluorination allows the conversion of methyl sorbate into the 6-fluoro analogue which undergoes sequential asymmetric dihydroxylation reactions. A range of 6-deoxy-6- fluorosugars were prepared by using different combinations of ligands. While the enantiomeric excesses obtained were comparable to those from other 6-substituted sorbates, the regioselectivity of dihydroxylation was moderate, with both 2,3- and 4,5-diols being obtained. A successful temporary persilylation strategy was evolved to convert the products of dihydroxylation rapidly to the fluorosugars 6-deoxy-6-fluoro-l-idose, 6-fluoro-l-fucose and 6-deoxy-6-fluoro-d-galactose, which were obtained in overall yields of 4%, 6% and 8% from methyl 6-fluoro-hexa-2E,4E-dienoate 6.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | biochemistry,physical and theoretical chemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology Faculty of Science > School of Biological Sciences |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 06 Sep 2024 13:35 |
| Last Modified: | 25 Sep 2024 18:07 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96601 |
| DOI: | 10.1039/b815342f |
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