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1984•Chemistry LettersRequires access

TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE (TRIMETHYLSILYL TRIFLATE) AS AN EXCELLENT GLYCOSIDATION REAGENT FOR ANTHRACYCLINE SYNTHESIS. SIMPLE AND EFFICIENT SYNTHESIS OF OPTICALLY PURE 4-DEMETHOXYDAUNORUBICIN

Yoshikazu Kimura, M. SUZUKI, Teruyo Matsumoto, Rumiko Abe, Shiro Terashima

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Abstract

Abstract The title reagent was found to effect the glycosidation of (+)-4-demethoxyanthracyclinones with N-trifluoroacetyl-1,4-di-O-p-nitrobenzoyl-l-daunosamine, giving the ot-glycosides in 99% yields. Sequential deprotections of the glycoside readily afforded optically pure (+)-4-demethoxydaunorubicin.

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What this paper is about

Abstract The title reagent was found to effect the glycosidation of (+)-4-demethoxyanthracyclinones with N-trifluoroacetyl-1,4-di-O-p-nitrobenzoyl-l-daunosamine, giving the ot-glycosides in 99% yields. Sequential deprotections of the glycoside readily afforded optically pure (+)-4-demethoxydaunorubicin.

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OpenAlex reports 41 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

Abstract The title reagent was found to effect the glycosidation of (+)-4-demethoxyanthracyclinones with N-trifluoroacetyl-1,4-di-O-p-nitrobenzoyl-l-daunosamine, giving the ot-glycosides in 99% yields. Sequential deprotections of the glycoside readily afforded optically pure (+)-4-demethoxydaunorubicin.

Key concepts: Chemistry, Trimethylsilyl trifluoromethanesulfonate, Trifluoromethanesulfonate, Trimethylsilyl, Reagent, Organic chemistry, Optically active, Anthracycline

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TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE (TRIMETHYLSILYL TRIFLATE) AS AN EXCELLENT GLYCOSIDATION REAGENT FOR ANTHRACYCLINE SYNTHESIS. SIMPLE AND EFFICIENT SYNTHESIS OF OPTICALLY PURE 4-DEMETHOXYDAUNORUBICIN — Research Paper | ScholarLens