Stereoselective synthesis of anomers of 5-substituted 2'-deoxyuridines.

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The substitution reaction of 5-substituted 2,4-bis(trimethylsilyloxy)pyrimidines with 3,5-bis(O-p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride was investigated. In the presence of p-nitrophenol, β anomers were formed stereoselectively, whereas the addition of organic bases brought forth stereoselective formation of α anomers. Stereoselectivity of the reaction depends on the substituents at 5-position of disilylpyrimidines, additives, and the concentration of each reagent. The α and β anomers of 5-substituted 2′-deoxy-uridines were synthesized through the deacylation of α and β anomers of 5-substituted 3′,5′-di-O-(p-chlorobenzoyl)-2′-deoxyuridines.
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