The newest member of the family of chloralose: Synthesis of β -ribochloralose and some derivatives
| dc.contributor.author | Ay K. | |
| dc.contributor.author | Halay E. | |
| dc.date.accessioned | 2025-04-10T11:14:13Z | |
| dc.date.available | 2025-04-10T11:14:13Z | |
| dc.date.issued | 2013 | |
| dc.description.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. © 2013 Kadir Ay and Erkan Halay. | |
| dc.identifier.DOI-ID | 10.1155/2013/748161 | |
| dc.identifier.uri | http://hdl.handle.net/20.500.14701/50188 | |
| dc.title | The newest member of the family of chloralose: Synthesis of β -ribochloralose and some derivatives | |
| dc.type | Article |