An unusual acetonide group migration
Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S N2 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. © 2003 Elsevier Ltd. All rights reserved.
Saksena, AK; Girijavallabhan, VM; Puar, MS; Pramanik, BN; Das, PR; McPhail, AT
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