223527-75-1Relevant academic research and scientific papers
Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide
Smelt, Kathryn H.,Harrison, Amanda J.,Biggadike, Keith,Mueller, Mathias,Prout, Keith,Watkin, David J.,Fleet, George W. J.
, p. 3259 - 3262 (1999)
Photobromination of the rigid, aza-bicyclic fucose mimic 3 gave a reactive glycosyl type bromide 7 as a divergent intermediate for the synthesis of both 7-0 and 7-N linked bycyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydrogenation gave a stable monoalkyl triazene 5, the structure of which was established by-X-ray crystallographic analysis. Hydrolysis of 7 allowed access to a monocyelic L-fucose mimic with a nitrogen substituent at C-5.
