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
来源：
JOURNAL OF CARBOHYDRATE CHEMISTRY | 1990年 / 9卷 / 04期
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.
引用
收藏
页码：479 / 499
页数：21
相关论文
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 [J].
BASHYAL, BP ;
CHOW, HF ;
FELLOWS, LE ;
FLEET, GWJ .
TETRAHEDRON, 1987, 43 (02) :415-422
[2]   SELECTIVE L-SORBOSE AZIDATION - APPLICATION TO RAPID 1-DEOXYNOJIRIMYCIN SYNTHESIS [J].
BEAUPERE, D ;
STASIK, B ;
UZAN, R ;
DEMAILLY, G .
CARBOHYDRATE RESEARCH, 1989, 191 (01) :163-166
[3]   TOTAL SYNTHESES OF (+)-CASTANOSPERMINE AND (+)-DEOXYNOJIRIMYCIN [J].
BERNOTAS, RC ;
GANEM, B .
TETRAHEDRON LETTERS, 1984, 25 (02) :165-168
[4]   EFFICIENT PREPARATION OF ENANTIOMERICALLY PURE CYCLIC AMINOALDITOLS, TOTAL SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN [J].
BERNOTAS, RC ;
GANEM, B .
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 [J].
CRAMER, F ;
OTTERBACH, H ;
SPRINGMANN, H .
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 [J].
FLEET, GWJ ;
FELLOWS, LE ;
SMITH, PW .
TETRAHEDRON, 1987, 43 (05) :979-990
[9]   INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].
GRUTERS, RA ;
NEEFJES, JJ ;
TERSMETTE, M ;
DEGOEDE, REY ;
TULP, A ;
HUISMAN, HG ;
MIEDEMA, F ;
PLOEGH, HL .
NATURE, 1987, 330 (6143) :74-77
[10]   SUGAR LACTAMS .3. SYNTHESIS OF 5- 6- AND 7-MEMBERED ANALOGS [J].
HANESSIAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :675-+
1234