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Journal of Carbohydrate Chemistry Volume 20, 2001 - Issue 1
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Original Articles

SYNTHESIS OF (6-2H)- AND 6-DEOXY-6-FLUORO-L-GALACTOSE DERIVATIVES1

Meinolf Brackhagen Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstra βe 9, Rostock, 18055, Germany
,
Hanna Boye Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstra βe 9, Rostock, 18055, Germany
&
Christian Vogel Department of Chemistry, Division of Organic Chemistry, University of Rostock, Buchbinderstra βe 9, Rostock, 18055, GermanyCorrespondence[email protected]
Pages 31-43 | Received 28 Jun 2000, Accepted 09 Nov 2000, Published online: 11 Dec 2006
 
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Abstract

The selective oxidation of trimethylsilylated D-galactose diethyl dithioacetal using Collins reagent provided the corresponding D-galacto-hexo-dialdo dithioacetal. Successive acid hydrolysis, isopropylidenation, and cleavage of the dithioacetal group gave the 1,2;3,4-di- O-isopropylidene-L-galacto-hexodialdo-1,5-pyranose as a key intermediate for the synthesis of 6-fluoro-and 6-deutero-substituted L-fucose derivatives.

1 Dedicated to Professor Peter Köll on the Occasion of His 60th Birthday.

ACKNOWLEDGMENTS

The authors are grateful to the Deutschen Forschungsgemeinschaft as well as the Fonds der Chemischen Industrie for financial support.

Notes

1 Dedicated to Professor Peter Köll on the Occasion of His 60th Birthday.

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