A series of novel guanidinoglycosides was successfully synthesized.
This was accomplished with the use of Mitsunobu conditions as a
strategy to convert the glycopyranose anomeric hydroxy group to
give the corresponding substituted masked guanidines in high yields.
Subsequent deprotection and coupling with Fmoc protected β-amino
acid, afforded a series of N,N′-substituted-methylisothioureas.
Cleavage of Fmoc followed by concomitant cyclization was achieved
with a catalytic amount of DBU to give the guanidinoglycosides.
guanidine - glycosides - Mitsunobu reaction - coupling - cyclization
