@article{961333ad2e644308ae349c7c89a29ee2,
title = "Syntheses of 1,5-dideoxy-1,5-imino-D-mannitol from D-mannose and from D-glucose",
abstract = "Unambiguous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.",
author = "Fleet, {G. W.J.} and Gough, {M. J.} and Shing, {T. K.M.}",
note = "Funding Information: efficient syntheses of deoxymannojirimycin from both D-mannose and D-glucose. References l)L.E.Fellows~ E.A.Bell. D.G.Lynn, and K.Nakanishi. J.Chem.Soc.,Chem.Commun.r1979.977. 2)U.Fuhrmann. E.Bause. G.Legler and H.Ploegh. Nature, 1984, 307, 755. 3)M.H.ALi, L.Hough and A.C.Richardson. J.Chem.Soc.rChem.Comm~I 1984, 447. 4)G.W.J.Fleetr M.J.Gough and P.W.Smith, Tetrahedron Lett., 1984,25,1853. S)G.Kinast and M.Schedel, Angew.Chem.Int.Ed., 1981r201805. - 6)K.Leonteinr B.Lindberg and J.Lonngren. Acta Chem.Eand. CB). 1982,36.515. 7)J.S.Brimacombe. F.Hunedy and L.C.N.Tucker, J.Chem.Soc.C, 1968.1381, 8)Only the enantiomer of (5) is ,known: m-p. 13/-l~8{"}, R.E.Ireland and J.P.Velvert. Can.J.Chem.. 1981,59,572. 9)Satisfactory spectral and/or analytical data were obtained lO)S.Czernecki. C.Georgoulis and C.Provelenghiou, Tetrahedron ll)A.Liptak. I.Jodal and P.Nanasi, Carbohydr.Res.,-(5 44 1 12)This work was supported by a SERC postdoctoral fello;SFiip'to CTKMS) and a SERC postgraduate award (to MJG).",
year = "1984",
doi = "10.1016/0040-4039(84)80058-1",
language = "English",
volume = "25",
pages = "4029--4032",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "36",
}