Synthesis of 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol, a novel analogue of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, via an Amadori rearrangement of 5-azido-5-deoxy-D-glucofuranose

被引:22
作者
Wrodnigg, TM
Stutz, AE
Withers, SG
机构
[1] GRAZ UNIV,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA
[2] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER,BC V6T 1Z1,CANADA
关键词
D O I
10.1016/S0040-4039(97)01198-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-dibenzylamino-1,5-dideoxy-D-fructopyranose, the new 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and excellent overall yield. Likewise, other amines and/or other 5-modified hexofuranoses can be used to advantage. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to 1-aminodeoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5463 / 5466
页数:4
相关论文
共 7 条
[1]   A NOVEL SYNTHETIC APPLICATION OF GLUCOSE-ISOMERASE - QUANTITATIVE CONVERSION OF D-GLUCOFURANOSE AND L-IDOFURANOSE DERIVATIVES MODIFIED AT POSITION 5 INTO THE CORRESPONDING D-FRUCTOPYRANOSES AND L-SORBOPYRANOSES [J].
BERGER, A ;
DERAADT, A ;
GRADNIG, G ;
GRASSER, M ;
LOW, H ;
STUTZ, AE .
TETRAHEDRON LETTERS, 1992, 33 (47) :7125-7128
[2]   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 [J].
DAX, K ;
GAIGG, B ;
GRASSBERGER, V ;
KOLBLINGER, B ;
STUTZ, AE .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (04) :479-499
[3]  
deRaadt A, 1997, TOP CURR CHEM, V187, P157
[4]   THE AMADORI REARRANGEMENT [J].
HODGE, JE .
ADVANCES IN CARBOHYDRATE CHEMISTRY, 1955, 10 :169-205
[5]   2,5-DIDEOXY-2,5-IMINO-D-MANNITOL AND -D-GLUCITOL - 2-STEP BIOORGANIC SYNTHESES FROM 5-AZIDO-5-DEOXY-D-GLUCOFURANOSE AND -L-IDOFURANOSE - EVALUATION AS GLUCOSIDASE INHIBITORS AND APPLICATION IN AFFINITY PURIFICATION AND CHARACTERIZATION OF INVERTASE FROM YEAST [J].
LEGLER, G ;
KORTH, A ;
BERGER, A ;
EKHART, C ;
GRADNIG, G ;
STUTZ, AE .
CARBOHYDRATE RESEARCH, 1993, 250 (01) :67-77
[6]   BOVINE N-ACETYL-BETA-D-GLUCOSAMINIDASE - AFFINITY PURIFICATION AND CHARACTERIZATION OF ITS ACTIVE-SITE WITH NITROGEN CONTAINING ANALOGS OF N-ACETYLGLUCOSAMINE [J].
LEGLER, G ;
LULLAU, E ;
KAPPES, E ;
KASTENHOLZ, F .
BIOCHIMICA ET BIOPHYSICA ACTA, 1991, 1080 (02) :89-95
[7]   INHIBITION OF N-ACETYLGLUCOSAMINYLTRANSFER ENZYMES - CHEMICAL-ENZYMATIC SYNTHESIS OF NEW 5-MEMBERED ACETAMIDO AZASUGARS [J].
TAKAOKA, Y ;
KAJIMOTO, T ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4809-4812