A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE

Journal article

Deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol] may be prepared in moderate amounts in an overall yield of 35% 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. © 1989.

Authors: Fleet, G; Ramsden, N; Witty, D

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 45
• Issue: 1
• Pages: 327-336
• Publication date: 1989-01-01
• DOI: 10.1016/0040-4020(89)80060-2
• ISSN: 0040-4020
• Language: English