A general and efficient route to 3'-deoxy-3'-N-, S-, and C-substituted altropyranosyl thymines from 2',3'-O-anhydro-mannopyranosylthymine

Deshpande, Sachin G. ; Pathak, Tanmaya (2007) A general and efficient route to 3'-deoxy-3'-N-, S-, and C-substituted altropyranosyl thymines from 2',3'-O-anhydro-mannopyranosylthymine Tetrahedron, 63 (3). pp. 602-608. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tet.2006.11.025

Abstract

An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene-β-D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-β-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3'-deoxy-3'-substituted altropyranosyl thymines.

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