A direct synthetic approach to uracil anhydrothionucleoside derivatives

Nouria A Al-Awadi; Yehia A Ibrahim; Maher R Ibrahim

doi:10.1016/j.carres.2009.09.006

A direct synthetic approach to uracil anhydrothionucleoside derivatives

Carbohydr Res. 2009 Nov 23;344(17):2322-8. doi: 10.1016/j.carres.2009.09.006. Epub 2009 Sep 16.

Authors

Nouria A Al-Awadi¹, Yehia A Ibrahim, Maher R Ibrahim

Affiliation

¹ Chemistry Department, Faculty of Science, Kuwait University, PO Box 5969, Safat 13060, Kuwait.

PMID: 19818434
DOI: 10.1016/j.carres.2009.09.006

Abstract

Direct conversion of peracylated N(1)-(beta-D-glucopyranosyl)-2-thiouracil derivatives into the corresponding anhydrothionucleosides has been studied under various conditions including: gas-phase pyrolysis, heating without a solvent, and by heating in a solvent of high boiling point (DPE) in the presence of a base (DABCO) and reaction in a microwave reactor. Heating at 210-220 degrees C was found to give the best yield of a single isomer. The structures of the new anhydrothionucleosides were confirmed by NMR techniques.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Thioglucosides / chemistry
Thiouridine / analogs & derivatives*
Thiouridine / chemical synthesis*

Substances

Thioglucosides
Thiouridine