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Photobromination of a bicyclic mimic of α-L-fucose; components for a combinatorial library of rigid fucose analogues

✍ Scribed by Kathryn H. Smelt; Yves Blériot; Keith Biggadike; Sean Lynn; Alexandra L. Lane; David J. Watkin; George W.J. Fleet

Book ID
104261171
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
309 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Photobromination of a rigid bicyclic ~t-L-fucose analogue, affords a single crystalline monobromide, the structure of which is confirmed by X-ray crystallography. Displacement of this bromide with azide proceeds with inversion to a single crystalline azide, which on reduction leads to an amine and thence to a range of novel substituted rigid ~-L-fucose derivatives. Hydrolysis of the bromide leads to two isomenc alcohols via an acetate migration. Both the bromide and amine may prove to be useful intermediates for the generation of libraries of mimics of L-fucose.

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