Synthesis of 2′,3′-Dideoxy-2′-Fluorokanamycin A
作者:
Tsutomu Tsuchiya,
Yoshiaki Takahashi,
Makoto Endo,
Sumio Umezawa,
Hamao Umezawa,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 4
页码: 587-611
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508082678
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
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 Na2S2O4was fluorinated with the DAST reagent to give methyl 4,6-O-benzylidene-2,3-dideoxy-2-fluoro-β-D-ribo-hexopyranoside (7). Successive treatment of7with NBS, NaN3and SOBr2gave13. The structure of the final product (23) was determined by the1H and19F and shift-correlated 2D NMR spectra.
点击下载:
PDF (951KB)
返 回