Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose

Journal article

Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (4), readily available from D-glucose, is a common intermediate in the enantiospecific syntheses of deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol](l), fagomine [1,2,5-trideoxy-1,5-imino-D-arabino hexitol] (2) and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (3); these syntheses establish the absolute configurations of (2) and (3). © 1985.

Authors: Fleet, G; Smith, P

• Journal: Tetrahedron Letters
• Volume: 26
• Issue: 11
• Pages: 1465-1468
• Publication date: 1985-01-01
• DOI: 10.1016/S0040-4039(00)99073-7
• ISSN: 0040-4039
• Language: English