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An unusual acetonide group migration

✍ Scribed by Anil K. Saksena; Viyyoor M. Girijavallabhan; Mohindar S. Puar; Birendra N. Pramanik; Pradip R. Das; Andrew T. McPhail

Book ID
104254334
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
151 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K 2 CO 3 did not provide the product of S N 2 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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