Synthesis of nojirimycinyl C-(L)-Serine

Ozonolysis of C-allyl nojirimycin 5 furnished aldehyde 6; ensuing Wittig-Ho rner reaction with glycine derived phosphonate 9 afforded alpha-acylaminoac rylate 10. Concomitant hydrogenation of the C=C double bond and hydrogenoly tic cleavage of the benzyloxycarbonyl protective group gave mainly the desi red nojirimycinyl C-(L)-serine derivative (L)-11, which was transformed int o suitable building blocks for the synthesis of novel glycopeptides. The co nfiguration of (L)-11 was assigned with the help of the Dale-Mosher method.