Nucleophilic displacement reactions in carbohydrates. Part XV. Displacements with 1,2:5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-β-L-talofuranose
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 11,p. 1632-1635
- https://doi.org/10.1039/j39700001632
Abstract
1,2:5,6-Di-O-isopropylidene-β-L-talofuranose (6) has been synthesised by oxidation of 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (4) and reduction of the resulting ketone (5). The endo-sulphonyloxy-group of 1,2:5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-β-L-talofuranose (7) was readily displaced with benzoate, azide, and fluoride ions to give the corresponding 3-substituted L-idose derivatives. The last displacement provided a convenient synthesis of 3-deoxy-3-fluoro-1,2:5,6-di-O-isopropylidene-β-L-idofuranose (11).Keywords
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