Partial Protection of Carbohydrate Derivatives. Part 13.1Chemical Conversion of Kanamycin A Into 2′-Deoxykanamycin A, 2′-Epi-Kanamycin A, and 2′-Epi-Kanamycin B
作者:
Nobuo Sakairi,
Toshio Yoneta,
Dalilur Rahman,
Yoshiharu Ishido,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1984)
卷期:
Volume 3,
issue 1
页码: 51-65
ISSN:0732-8303
年代: 1984
DOI:10.1080/07328308408057897
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Hydrazinolyses of hexa-0-benzoyl-tetra-N-benzyloxycarbonyl-andN-ethoxycarbonylkanamycin A were performed and found to be sufficiently regioselective to give the corresponding 2′-hydroxyl derivatives in good yields under controlled conditions. The products were converted into the corresponding 2′-triflates, which were then subjected to nucleophilic substitution reactions with sodium benzenethioxide, sodium benzoate, and sodium azide to give the correspondingd-mannopyranosyl derivatives in good yields. Deprotection of the phenylthio (10) and azido (12) derivatives, and hydrogenolysis, gave 2′-deoxykankmycin A and 2′-epi-kanamycin B, respectively. Moreover, deprotection of the benzoyl compound11gave 2′-epi-kanamycin A.
点击下载:
PDF (557KB)
返 回