SIMPLE SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL(1-DEOXYNOJIRIMYCIN) AND 1,6-DIDEOXY-1,6-IMINO-D-GLUCITOL FROM D-GLUCOFURANURONO-6,3-LACTONE

被引:76
作者
DAX, K
GAIGG, B
GRASSBERGER, V
KOLBLINGER, B
STUTZ, AE
机构
[1] Institut für Organische Chemie, Technische Universität Graz, GRAZ A-8010
关键词
D O I
10.1080/07328309008543848
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
l,5-Dideoxy-l,5-imino-D-glucitol (1-deoxynojirimycin) and 1,6-dideoxy-l,6-imino-D-glucitol were synthesised by simple sequences in seven and six steps, respectively, from D-glucofuranurono-6,3-lactone. Attempts to improve the yield of the crucial regio- and stereospecific introduction of azide into position 5 of suitable derivatives of this substrate are described. © 1990, Taylor & Francis Group, LLC. All rights reserved.
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页码:479 / 499
页数:21
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共 34 条
  • [1] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
    BASHYAL, BP
    CHOW, HF
    FELLOWS, LE
    FLEET, GWJ
    [J]. TETRAHEDRON, 1987, 43 (02) : 415 - 422
  • [2] SELECTIVE L-SORBOSE AZIDATION - APPLICATION TO RAPID 1-DEOXYNOJIRIMYCIN SYNTHESIS
    BEAUPERE, D
    STASIK, B
    UZAN, R
    DEMAILLY, G
    [J]. CARBOHYDRATE RESEARCH, 1989, 191 (01) : 163 - 166
  • [3] TOTAL SYNTHESES OF (+)-CASTANOSPERMINE AND (+)-DEOXYNOJIRIMYCIN
    BERNOTAS, RC
    GANEM, B
    [J]. TETRAHEDRON LETTERS, 1984, 25 (02) : 165 - 168
  • [4] EFFICIENT PREPARATION OF ENANTIOMERICALLY PURE CYCLIC AMINOALDITOLS, TOTAL SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN
    BERNOTAS, RC
    GANEM, B
    [J]. TETRAHEDRON LETTERS, 1985, 26 (09) : 1123 - 1126
  • [5] BROXTERMAN HJG, 1987, RECL TRAV CHIM PAY B, V106, P571
  • [6] EINE SYNTHESE DER 6-DESOXY-6-AMINO-GLUCOSE
    CRAMER, F
    OTTERBACH, H
    SPRINGMANN, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (02): : 384 - 391
  • [7] DAX K, 1981, LIEBIGS ANN CHEM, P1768
  • [8] SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE
    FLEET, GWJ
    FELLOWS, LE
    SMITH, PW
    [J]. TETRAHEDRON, 1987, 43 (05) : 979 - 990
  • [9] INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE
    GRUTERS, RA
    NEEFJES, JJ
    TERSMETTE, M
    DEGOEDE, REY
    TULP, A
    HUISMAN, HG
    MIEDEMA, F
    PLOEGH, HL
    [J]. NATURE, 1987, 330 (6143) : 74 - 77
  • [10] SUGAR LACTAMS .3. SYNTHESIS OF 5- 6- AND 7-MEMBERED ANALOGS
    HANESSIAN, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) : 675 - +