Skip to main content
Journal cover image

An unusual acetonide group migration

Publication ,  Journal Article
Saksena, AK; Girijavallabhan, VM; Puar, MS; Pramanik, BN; Das, PR; McPhail, AT
Published in: Tetrahedron Letters
September 15, 2003

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.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

September 15, 2003

Volume

44

Issue

38

Start / End Page

7201 / 7204

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Saksena, A. K., Girijavallabhan, V. M., Puar, M. S., Pramanik, B. N., Das, P. R., & McPhail, A. T. (2003). An unusual acetonide group migration. Tetrahedron Letters, 44(38), 7201–7204. https://doi.org/10.1016/S0040-4039(03)01758-1
Saksena, A. K., V. M. Girijavallabhan, M. S. Puar, B. N. Pramanik, P. R. Das, and A. T. McPhail. “An unusual acetonide group migration.” Tetrahedron Letters 44, no. 38 (September 15, 2003): 7201–4. https://doi.org/10.1016/S0040-4039(03)01758-1.
Saksena AK, Girijavallabhan VM, Puar MS, Pramanik BN, Das PR, McPhail AT. An unusual acetonide group migration. Tetrahedron Letters. 2003 Sep 15;44(38):7201–4.
Saksena, A. K., et al. “An unusual acetonide group migration.” Tetrahedron Letters, vol. 44, no. 38, Sept. 2003, pp. 7201–04. Scopus, doi:10.1016/S0040-4039(03)01758-1.
Saksena AK, Girijavallabhan VM, Puar MS, Pramanik BN, Das PR, McPhail AT. An unusual acetonide group migration. Tetrahedron Letters. 2003 Sep 15;44(38):7201–7204.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

September 15, 2003

Volume

44

Issue

38

Start / End Page

7201 / 7204

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry