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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Fluorination (at C5) of Some Derivatives of D-Glucose

Brian W. Skelton, Robert V. Stick, Keith A. Stubbs, Andrew G. Watts and Allan H. White

Australian Journal of Chemistry 57(4) 345 - 353
Published: 02 April 2004

Abstract

The photobromination of various per-esters of β-D-glucopyranose and α- and β-D-glucopyranosyl fluoride has yielded 5-bromo derivatives capable of conversion into the corresponding 5-fluorides. The best reagent for this conversion was found to be silver tetrafluoroborate in ether/dichloromethane. The single-crystal X-ray structure determination of penta-O-benzoyl-5-fluoro-α-L-idopyranose is presented.

As well, various approaches to 5-fluoro glycopyranosides have been developed. The photobromination of phenyl tetra-O-acetyl-β-D-glucopyranoside, followed by fluorination and protecting group removal gave phenyl 5-fluoro-β-D-glucopyranoside. The photobromination of penta-O-acetyl-β-D-glucopyranose, followed by hydro- lysis and treatment with methanol, gave a hemiacetal that was converted via treatment with diethylaminosulfur trifluoride followed by protecting group removal into methyl 5-fluoro-β-D-glucopyranoside. Methyl 2,3,4-tri-O-benzyl-6-deoxy-α- and -β-D-xylo-hex-5-enosides were converted into their corresponding epoxides with either dimethyldioxirane or 3-chloroperbenzoic acid; subsequent treatment with hydrogen fluoride/pyridine then generated the 5-fluoro glycopyranosides as the major products. A single-crystal X-ray structure determination of 1,6-anhydro-2,3,4-tri-O-benzyl-5-hydroxy-β-L-idose is presented.

Keywords: carbohydrates — fluorinated substituents — fluorination — photobromination — synthesis (org.)

https://doi.org/10.1071/CH03288

© CSIRO 2004

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