An unusual acetonide group migration |
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| Authors: | Anil K. Saksena Viyyoor M. GirijavallabhanMohindar S. Puar Birendra N. PramanikPradip R. Das Andrew T. McPhail |
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| Affiliation: | a Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA
b Paul M. Gross Chemical Laboratories, Duke University, Durham, NC 27706, USA |
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| Abstract: | Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of SN2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and single crystal X-ray analysis. The desired product 2 could be ultimately obtained by Mitsunobu reaction of the alcohol 6 with 3-N-benzoyl uracil followed by basic hydrolysis. |
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