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  • Title: Regioselective syntheses of beta-N-linked glycoaminoacids and glycopeptides.
    Author: Katritzky AR, Narindoshvili T, Draghici B, Angrish P.
    Journal: J Org Chem; 2008 Jan 18; 73(2):511-6. PubMed ID: 18088141.
    Abstract:
    Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-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 beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by 1D and 2D NMR techniques for 3b.
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