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
✍ Scribed by Kathryn H. Smelt; Amanda J. Harrison; Keith Biggadike; Mathias Müller; Keith Prout; David J. Watkin; George W.J. Fleet
- Book ID
- 104261172
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 302 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-8 yinked 1 cosyl bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydro enation gave a stable monoalkyl tiazene 5, the structure of which was established by analysis. Hydrol %-ray crystallographic sis of 7 allowed access to a monocyclic L-fucose mimic with a mtrogen substituent at C-.