An unusual acetonide group migration

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Saksena, AK; Girijavallabhan, VM; Puar, MS; Pramanik, BN; Das, PR; McPhail, AT

Published Date

  • September 15, 2003

Published In

Volume / Issue

  • 44 / 38

Start / End Page

  • 7201 - 7204

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/S0040-4039(03)01758-1

Citation Source

  • Scopus