615286-30-1Relevant academic research and scientific papers
An unusual acetonide group migration
Saksena, Anil K.,Girijavallabhan, Viyyoor M.,Puar, Mohindar S.,Pramanik, Birendra N.,Das, Pradip R.,McPhail, Andrew T.
, p. 7201 - 7204 (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.
