A STEREOSELECTIVE ROUTE TO THE SUGAR-CINNAMATE UNIT OF HYGROMYCIN-A

被引:19
作者
BUCHANAN, JG
HILL, DG
WIGHTMAN, RH
BODDY, IK
HEWITT, BD
机构
[1] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND
[2] AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
关键词
D O I
10.1016/0040-4020(95)00262-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various aryl 6-deoxy-5-keto-beta-D-arabino-hexofuranosides including one (42) corresponding to the sugar-cinnamate unit of Hygromycin A (1) have been synthesized by a method in which 6-deoxy-beta-D-glucofuranosides are first prepared, followed by configurational inversion at positions 2 and 3 via 23-anhydro-6-deoxy-beta-D-mamofuranosyl intermediates.
引用
收藏
页码:6033 / 6050
页数:18
相关论文
共 32 条
[1]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 :27-66
[3]   PHENYL GLYCOFURANOSIDES .1. SYNTHESIS OF PHENYL BETA-D-XYLOFURANOSIDE AND PHENYL ALPHA-L-ARABINOFURANOSIDE [J].
BORJESON, H ;
LINDBERG, B ;
JERKEMAN, P .
ACTA CHEMICA SCANDINAVICA, 1963, 17 (06) :1705-&
[4]  
BUCHANAN JG, 1972, SELECTIVE ORGANIC TR, V2, P34
[5]   TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A [J].
CHIDA, N ;
OHTSUKA, M ;
NAKAZAWA, K ;
OGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2976-2983
[6]   CONFORMATIONS OF FURANOSIDES - C-13 NUCLEAR MAGNETIC-RESONANCE STUDY [J].
CYR, N ;
PERLIN, AS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (18) :2504-2511
[7]  
GREENE TW, 1981, PROTECTIVE GROUPS OR
[8]   NOVEL SYNTHESIS OF ARYL GLYCOSIDES [J].
GRYNKIEWICZ, G .
CARBOHYDRATE RESEARCH, 1977, 53 (01) :C11-C12
[9]  
HANSSON C, 1976, SYNTHESIS-STUTTGART, P191
[10]   SIMPLE SYNTHESIS OF GLYCOSYL FLUORIDES [J].
HAYASHI, M ;
HASHIMOTO, S ;
NOYORI, R .
CHEMISTRY LETTERS, 1984, (10) :1747-1750