Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose
作者： George W.J. Fleet , Paul W. Smith
DOI: 10.1016/S0040-4039(00)99073-7
关键词:
摘要: Abstract 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 establish absolute configurations (3).
elsevier.com
sci-hub.se 参考文章(10)
A D Elbein, M Mitchell, B A Sanford, L E Fellows, S V Evans, The pyrrolidine alkaloid, 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine, inhibits glycoprotein processing. Journal of Biological Chemistry. ,vol. 259, pp. 12409- 12413 ,(1984) , 10.1016/S0021-9258(18)90761-1
Linda E. Fellows, E. Arthur Bell, David G. Lynn, Frank Pilkiewicz, I. Miura, Koji Nakanishi, Isolation and structure of an unusual cyclic amino alditol from a legume Journal of The Chemical Society, Chemical Communications. pp. 977- 978 ,(1979) , 10.1039/C39790000977
Jack E. Baldwin, Rules for ring closure Journal of the Chemical Society, Chemical Communications. pp. 734- 736 ,(1976) , 10.1039/C39760000734
S.V. Evans, L.E. Fellows, T.K.M. Shing, G.W.J. Fleet, Glycosidase inhibition by plant alkaloids which are structural analogues of monosaccharides Phytochemistry. ,vol. 24, pp. 1953- 1955 ,(1985) , 10.1016/S0031-9422(00)83099-X
André Welter, Joseph Jadot, Gaston Dardenne, Michel Marlier, Jean Casimir, 2,5-Dihydroxymethyl 3,4-dihydroxypyrrolidine dans les feuilles de Derris elliptica Phytochemistry. ,vol. 15, pp. 747- 749 ,(1976) , 10.1016/S0031-9422(00)94435-2
S. Czernecki, C. Georgoulis, C. Provelenghiou, Nouvelle methode de benzylation d'hydroxyles glucidiques encombres Tetrahedron Letters. ,vol. 17, pp. 3535- 3536 ,(1976) , 10.1016/S0040-4039(00)71351-7
Z.F. Mahmoud, F.F. Kassem, N.A. Abdel-Salam, C. Zdero, Sesquiterpene lactones from Lactuca sativa Phytochemistry. ,vol. 25, pp. 747- 748 ,(1986) , 10.1016/0031-9422(86)88039-6
G.W.J. Fleet, M.J. Gough, P.W. Smith, Enantiospecific Synthesis of Swainsonine, (1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine, from D-mannose Tetrahedron Letters. ,vol. 25, pp. 1853- 1856 ,(1984) , 10.1016/S0040-4039(01)90059-0
Günter Legler, Elisabeth Jülich, Synthesis of 5-amino-5-deoxy-d-mannopyranose and 1,5-di-deoxy-1,5-imino-d-mannitol, and inhibition of α- and β-d-mannosidases Carbohydrate Research. ,vol. 128, pp. 61- 72 ,(1984) , 10.1016/0008-6215(84)85084-3
HIROMICHI SAEKI, TADAHIRO IWASHIGE, EIJI OHKI, Conversion of d-glucofuranose to l-arabino-hexofuranoside. Chemical & Pharmaceutical Bulletin. ,vol. 16, pp. 1040- 1047 ,(1968) , 10.1248/CPB.16.1040