Tetrahedron p. 327 - 336 (1989)
Update date:2022-08-04
Topics:
Fleet, George W. J.
Ramsden, Nigel G.
Witty, David R.
Deoxymannojirimycin <1,5-dideoxy-1,5-imino-D-mannitol> may be prepared in moderate amounts in an overall yield of 35percent in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar.A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported.
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