Synthesis of 2?,3?-Dideoxy-2?-Fluorokanamycin A
- 1 December 1985
- journal article
- research article
- Published by Taylor & Francis Ltd in Journal of Carbohydrate Chemistry
- Vol. 4 (4), 587-611
- https://doi.org/10.1080/07328308508082678
Abstract
2′,3′-Dideoxy-2′-fluorokanamycin A (23) was prepared by condensation of 6-azido-4-0-benzoyl-2,3,6-trideoxy-2-fluoro-α-D-ribo-hexopyranosyl bromide (13) and a protected disaccharide (19). Methyl 4,6-0-benzylidene-3-deoxy-β-D-arabino-hexopyranoside (5) prepared from methyl 4,6-0-benzylidene-3-chloro-3-deoxy-β-D-allo-hexopyranoside (1) by oxidation with pyridinium chlorochromate followed by reduction with Na2 S2O4 was fluorinated with the DAST reagent to give methyl 4,6-O-benzylidene-2,3-dideoxy-2-fluoro-β-D-ribo-hexopyranoside (7). Successive treatment of 7 with NBS, NaN3 and SOBr2 gave 13. The structure of the final product (23) was determined by the 1H and 19F and shift-correlated 2D NMR spectra.Keywords
This publication has 14 references indexed in Scilit:
- Reaction of α-Haloketones with Na2S2O4. A Convenient Dehalogenation ProcedureSynthetic Communications, 1982
- ENHANCED EFFECT OF SPRAY-DRIED POTASSIUM FLUORIDE ON FLUORINATIONChemistry Letters, 1981
- One-step Conversion of vicinal Diols into Olefins, using a Novel Reagent SystemSynthesis, 1979
- Drifluor reagents: non-hygroscopic sources of the fluoride ionJournal of the Chemical Society, Chemical Communications, 1978
- Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside by the Tipson-Cohen reactionCarbohydrate Research, 1976
- Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharidesJournal of the American Chemical Society, 1975
- Synthesis of Paratose (3,6-Dideoxy-D-ribo-hexose) and Tyvelose (3,6-DiAeoxy-D-arabino-hexose)Canadian Journal of Chemistry, 1971
- Reaction of O-benzylidene sugars with N-bromosuccinimide. II. Scope and synthetic utility in the methyl 4,6-0-benzylidenehexopyranoside seriesThe Journal of Organic Chemistry, 1969
- Reaction of O-benzylidene sugars with N-bromosuccinimide. III. Applications to the synthesis of aminodeoxy and deoxy sugars of biological importanceThe Journal of Organic Chemistry, 1969
- REACTIONS OF SUGAR CHLOROSULFATES: PART V. THE SYNTHESIS OF CHLORODEOXY SUGARSCanadian Journal of Chemistry, 1965