ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES

被引:426
作者
HALCOMB, RL [1 ]
DANISHEFSKY, SJ [1 ]
机构
[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511
关键词
D O I
10.1021/ja00199a028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
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页码:6661 / 6666
页数:6
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共 33 条
[1]   SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].
ADAM, W ;
CHAN, YY ;
CREMER, D ;
GAUSS, J ;
SCHEUTZOW, D ;
SCHINDLER, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803
[2]  
BAERTSCHI SW, 1988, J AM CHEM SOC, V110, P1988
[3]   EPOXIDATION BY DIMETHYLDIOXIRANE - ELECTRONIC AND STERIC EFFECTS [J].
BAUMSTARK, AL ;
VASQUEZ, PC .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3437-3439
[4]   EPOXIDATION OF ALKENES BY DIMETHYLDIOXIRANE - EVIDENCE FOR A SPIRO TRANSITION-STATE [J].
BAUMSTARK, AL ;
MCCLOSKEY, CJ .
TETRAHEDRON LETTERS, 1987, 28 (29) :3311-3314
[5]   STEREOCONTROLLED SYNTHESIS OF C-GLYCOSIDES BY REACTION OF ORGANOCUPRATES WITH PROTECTED 1,2-ANHYDRO SUGARS, AND THEIR TRANSFORMATION INTO 2-DEOXY-C-GLYCOSIDES [J].
BELLOSTA, V ;
CZERNECKI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) :199-200
[6]   On the unsaturated reduction products of sugar types and their transformations, I. On the issue of glucal. [J].
Bergmann, M ;
Schotte, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1921, 54 :440-455
[7]   STUDIES ON UNSATURATED SUGARS WITH PARTICULAR REFERENCE TO SYNTHESIS OF 6-DEOXY-6-FLUORO DERIVATIVES [J].
BLACKBURNE, ID ;
FREDERICKS, PM ;
GUTHRIE, RD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (02) :381-391
[8]  
BRIGL P, 1922, Z PHYSL CHEM, V122, P257
[9]   EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].
CURCI, R ;
FIORENTINO, M ;
TROISI, L ;
EDWARDS, JO ;
PATER, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760
[10]   FORMATION AND REACTIVITY OF DIOXIRANE INTERMEDIATES IN THE REACTION OF PEROXOANIONS WITH ORGANIC SUBSTRATES [J].
EDWARDS, JO ;
PATER, RH ;
CURCI, R ;
DIFURIA, F .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1979, 30 (01) :63-70