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Journal of Chemistry
Volume 2013 (2013), Article ID 748161, 7 pages
http://dx.doi.org/10.1155/2013/748161
Research Article

The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives

Department of Chemistry, Faculty of Arts and Sciences, Celal Bayar University, Campus of Muradiye, 45030 Manisa, Turkey

Received 8 February 2013; Revised 10 March 2013; Accepted 11 March 2013

Academic Editor: Huu Hao Ngo

Copyright © 2013 Kadir Ay and Erkan Halay. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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.