Improved Stereoselective Synthesis of the β-Anomer of 1-[3,5-Bis-O-(p-chlorobenzoyl)-2-deoxy-d-ribofuranosyl]-5-iodo-2-pyrimidinone

The lack of stereochemical control has been a major hurdle in synthesizing β-nucleosides in large scale. This paper reports a study of the effects of different catalysts used in the synthesis of β-nucleosides. The effects of time and temperature on α- and β-anomers are illustrated in this paper. The...

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Bibliographic Details
Published in:Organic process research & development 1999-03, Vol.3 (2), p.135-138
Main Authors: Schure, Ralph, Mar, Aye Aye, Pease, Brian, Jones, Wyeth, Felt, Barb, Iyer, Mani S
Format: Article
Language:English
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Summary:The lack of stereochemical control has been a major hurdle in synthesizing β-nucleosides in large scale. This paper reports a study of the effects of different catalysts used in the synthesis of β-nucleosides. The effects of time and temperature on α- and β-anomers are illustrated in this paper. The yield and selectivity of the β-nucleoside have been improved vastly at temperatures between −30 and −40 °C and by using SnCl4 as the catalyst.
ISSN:1083-6160
1520-586X
DOI:10.1021/op980204o