Opening of 2',3'-O-anhydro-ring of 2',3'-O-anhydro-lyxo-uridine by alkyl- and arylamines. Easy syntheses and preparative uses of 2'-deoxy-2'-alkylamino-xylo- and 3'-deoxy-3'-alkylamino-ara-uridines

Bera, Sanjib ; Pathak, Tanmaya ; Langley, Graham J. (1995) Opening of 2',3'-O-anhydro-ring of 2',3'-O-anhydro-lyxo-uridine by alkyl- and arylamines. Easy syntheses and preparative uses of 2'-deoxy-2'-alkylamino-xylo- and 3'-deoxy-3'-alkylamino-ara-uridines Tetrahedron, 51 (5). pp. 1459-1470. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(94)01040-7

Abstract

Contrary to the previous report (ref. 8), under controlled conditions alkylamines, both primary and secondary and arylamines, opened the epoxide ring of 1-(5-O-trityl-2,3-O-anhydro-β-D-lyxo-furanosyl)-uracil to produce 2'-deoxy-2'-alkylamino-xylo- and 3'-deoxy-3'-alkylamino-ara-uridines without causing any significant deglycosylation. To show the utility of these products, several modified uridine derivatives were synthesised.

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