A. Katritzky, T. Narindoshvili, B. Draghici
Jan 18, 2008
Citations
0
Influential Citations
21
Citations
Journal
Journal of Organic Chemistry
Abstract
Acylation of tetra-O-pivaloyl-β-d-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-α-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give β-N-glycoaminoacids 3a−d, (3c+3c‘) (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83−92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a−c similarly afforded β-N-glycodipeptides 5a−c (76−81%). Regiospecific β-N-linkage formation was established by 1D and 2D NMR techniques for 3b.