Tetrahedron p. 979 - 990 (1987)
Update date:2022-08-04
Topics:
Fleet, George W. J.
Fellows, L. E.
Smith, Paul W.
The value of methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside as a divergent intermediate for the preparation of polyhydroxylated piperidines is illustrated by the synthesis of deoxymannojirimycin (1,5-dideoxy-1,5-imino-D-mannitol), fagomine (1,5-imino-1,2,5-trideoxy-D-arabino-hexitol), deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol), 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol, 2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol, 2S,3R,4R,5R-trihydroxypipecolic acid and 2S,3R,4R,5S-trihydroxypipecolic acid.
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