Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses

Audrey Caravano, Robert A. Field, Jonathan M. Percy, Giuseppe Rinaudo, Ricard Roig, Kuldip. Singh

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Free radical bromination and nucleophilic fluorination allows the conversion of Me sorbate into the 6-fluoro analog which undergoes sequential asym. dihydroxylation reactions. A range of 6-deoxy-6-fluoro-sugars were prepd. 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 fluoro-sugars 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 Me 6-fluoro-hexa-2E,4E-dienoate.
LanguageUndefined/Unknown
Pages996-1008
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number5
DOIs
Publication statusPublished - 2009

Keywords

  • bromination
  • nucleophilic fluorination
  • ligands
  • dihydroxylation

Cite this

Caravano, A., Field, R. A., Percy, J. M., Rinaudo, G., Roig, R., & Singh, K. (2009). Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses. Organic and Biomolecular Chemistry, 7(5), 996-1008. https://doi.org/10.1039/b815342f
Caravano, Audrey ; Field, Robert A. ; Percy, Jonathan M. ; Rinaudo, Giuseppe ; Roig, Ricard ; Singh, Kuldip. / Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses. In: Organic and Biomolecular Chemistry. 2009 ; Vol. 7, No. 5. pp. 996-1008.
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abstract = "Free radical bromination and nucleophilic fluorination allows the conversion of Me sorbate into the 6-fluoro analog which undergoes sequential asym. dihydroxylation reactions. A range of 6-deoxy-6-fluoro-sugars were prepd. 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 fluoro-sugars 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 Me 6-fluoro-hexa-2E,4E-dienoate.",
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Caravano, A, Field, RA, Percy, JM, Rinaudo, G, Roig, R & Singh, K 2009, 'Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses' Organic and Biomolecular Chemistry, vol. 7, no. 5, pp. 996-1008. https://doi.org/10.1039/b815342f

Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses. / Caravano, Audrey; Field, Robert A.; Percy, Jonathan M.; Rinaudo, Giuseppe; Roig, Ricard; Singh, Kuldip.

In: Organic and Biomolecular Chemistry, Vol. 7, No. 5, 2009, p. 996-1008.

Research output: Contribution to journalArticle

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T1 - Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses

AU - Caravano, Audrey

AU - Field, Robert A.

AU - Percy, Jonathan M.

AU - Rinaudo, Giuseppe

AU - Roig, Ricard

AU - Singh, Kuldip.

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AB - Free radical bromination and nucleophilic fluorination allows the conversion of Me sorbate into the 6-fluoro analog which undergoes sequential asym. dihydroxylation reactions. A range of 6-deoxy-6-fluoro-sugars were prepd. 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 fluoro-sugars 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 Me 6-fluoro-hexa-2E,4E-dienoate.

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KW - ligands

KW - dihydroxylation

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