The newest member of the family of chloralose: Synthesis of β -ribochloralose and some derivatives

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. © 2013 kadir ay and erkan halay.