A Simple Method for Deprotection of the N- and O-Carbobenzoxy Groups and N-Methylation of the Desosamine Sugar Moiety of Ketolides

A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among...

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Published inJournal of antibiotics Vol. 58; no. 11; p. 679
Main Authors Iwaki, Tsutomu, Nomura, Takashi, Narukawa, Yukitoshi, Uotani, Koichi
Format Journal Article
LanguageEnglish
Published Tokyo Nature Publishing Group 01.11.2005
Subjects
Sugar
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Abstract A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among the ketolide derivatives prepared by this method, compound 7g with a quinoline-6-yl moiety showed potent activity against erythromycin-resistant pathogens as well as Haemophilus influenzae.
AbstractList A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among the ketolide derivatives prepared by this method, compound 7g with a quinoline-6-yl moiety showed potent activity against erythromycin-resistant pathogens as well as Haemophilus influenzae.
Author Iwaki, Tsutomu
Narukawa, Yukitoshi
Nomura, Takashi
Uotani, Koichi
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Title A Simple Method for Deprotection of the N- and O-Carbobenzoxy Groups and N-Methylation of the Desosamine Sugar Moiety of Ketolides
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