首页   按字顺浏览 期刊浏览 卷期浏览 Synthesis of 2′,3′-Dideoxy-2′-Fluorokanamycin A
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