121195-27-5Relevant articles and documents
A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
Fleet, George W. J.,Ramsden, Nigel G.,Witty, David R.
, p. 327 - 336 (2007/10/02)
Deoxymannojirimycin 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.