Abstract
Treatment of D‐ribose with chloral in the presence of acid catalyst gives 1,2‐O‐(S)‐trichloroethylidene‐α‐D‐ribofuranose (1) (β‐ribochloralose). Some derivatives of this product (1) were synthesized to be used as an intermediate in carbohydrate chemistry. Tricyclic orthoester structure (3, 77%) was obtained from the reaction of 1 with potassium t‐butoxide. This novel orthoester is expected to be useful as a glycosyl donor in the formations of new ribofuranoside units. 3‐O‐Methyl‐ribochloralose (5) was synthesized in 75% yield via the methylation of 1. 5‐O‐Tosyl‐ribochloralose (6, 61%) was prepared with monotosylation reaction of 1. Treatment of 6 with NaN3 in DMF gives a 5‐azido‐5‐deoxy‐ribochloralose (7) in 77% yield. The azidosugar (7) was reduced to 5‐amino‐5‐deoxy‐ribochloralose (8, 72%) with triphenylphosphine according to Staudinger’s reduction procedure.
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