Synthesis of an 1-azaglucose analogue with ring-oxygen retained.

被引:35
作者
Bach, P [1 ]
Bols, M [1 ]
机构
[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus, Denmark
关键词
D O I
10.1016/S0040-4039(99)00423-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the glucose analogue 4,5-dihydroxy-6-hydroxymethyl-tetrahydrooxazine (4) is reported for the first time. (C) 1999 Elsevier Science Lid. All rights reserved.
引用
收藏
页码:3461 / 3464
页数:4
相关论文
共 17 条
[1]   THE USE OF DICHLOROMALEIC AND BROMOMALEIC ANHYDRIDES IN THE SYNTHESIS OF LACTONES BY THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
BATCHELOR, MJ ;
MELLOR, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :985-995
[2]  
BEST WM, 1997, TOP CURR CHEM, V187, P197
[3]  
BLANDA G, ROYAL SOC CHEM CARB
[4]   1-azafagomine: A hydroxyhexahydropyridazine that potently inhibits enzymatic glycoside cleavage [J].
Bols, M ;
Hazell, RG ;
Thomsen, IB .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (06) :940-947
[5]   1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].
Bols, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8
[6]   AN IMINO-LINKED CARBA-DISACCHARIDE ALPHA-DEUTERIUM-MANNOSIDASE INHIBITOR [J].
COTTAZ, S ;
BRIMACOMBE, JS ;
FERGUSON, MAJ .
CARBOHYDRATE RESEARCH, 1993, 247 :341-345
[7]   Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions [J].
Defoin, A ;
Sarazin, H ;
Streith, J .
HELVETICA CHIMICA ACTA, 1996, 79 (02) :560-567
[8]   CONFIGURATIONALLY SELECTIVE TRANSITION-STATE ANALOG INHIBITORS OF GLYCOSIDASES - A STUDY WITH NOJIRITETRAZOLES, A NEW CLASS OF GLYCOSIDASE INHIBITORS [J].
ERMERT, P ;
VASELLA, A ;
WEBER, M ;
RUPITZ, K ;
WITHERS, SG .
CARBOHYDRATE RESEARCH, 1993, 250 (01) :113-128
[9]   Inhibitors of carbohydrate-processing enzymes: Design and synthesis of sugar-shaped heterocycles [J].
Ganem, B .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (07) :340-347
[10]   1-N-iminosugars:: Potent and selective inhibitors of β-glycosidases (vol 120, pg 3007, 1998) [J].
Ichikawa, Y ;
Igarashi, Y ;
Ichikawa, M ;
Suhara, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5854-5854