Synthesis of guanidines from azides: a general and straightforward methodology in carbohydrate chemistry.
The ability of the guanidinylating reagent N',N''-diBoc-N-triflyl-guanidine (GN-Tf) to react with in situ formed free amines from azides in carbohydrate scaffolds was explored. This reaction proved to be an efficient method to prepare guanidine derivatives in a one-pot manner with good to excellent yields, either with primary or secondary azides with different substitution patterns. Labile protecting groups such as benzyl ethers are not removed under these hydrogenolytic conditions.
Santana
Andrés G
AG
Instituto de Productos Naturales y Agrobiología del C.S.I.C., 38206 La Laguna Tenerife, Spain.
Francisco
Cosme G
CG
Suárez
Ernesto
E
González
Concepción C
CC
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D001386:Azides; D002241:Carbohydrates; D006146:Guanidines