HIGH-PRESSURE GLYCOSYLATIONS OF UNREACTIVE ALCOHOLS AND THE FORMATION OF N-GLYCOSYL COLLIDINIUM SALTS

被引:15
作者
DAUBEN, WG
KOHLER, P
机构
[1] Department of Chemistry, University of California, Berkeley
关键词
D O I
10.1016/0008-6215(90)80044-4
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
The yields of disaccharide glycosylation products in tetramethylammonium bromide or silver triflate-collidine activated reactions between hindered alcohols and glycosyl halides were not greatly affected when a pressure of 15 kbar was applied. The formation of orthoester products was greatly increased under pressure. When orthoester formation was not possible both disaccharides and the related N-glycosyl collidinium salts were found. © 1990.
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页码:47 / 56
页数:10
相关论文
共 28 条
[1]   KOENIGS-KNORR SYNTHESES OF SOME ALPHA-1 -] 2 AND BETA-1 -] 2 LINKED NITRO DISACCHARIDES .34. [J].
BAER, HH ;
FRECHET, JMJ ;
WILLIAMS, U .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (19) :3337-3342
[2]   THE SYNTHESIS OF TRI-TERT-BUTYLCARBINOL AND OTHER HIGHLY BRANCHED ALCOHOLS BY MEANS OF SODIUM [J].
BARTLETT, PD ;
SCHNEIDER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (01) :141-144
[3]   ANALYSIS OF MIXTURES OF N-OCTENES OCTALINS T-BUTYLCYCLOHEXENES OCTANOLS DECALOLS AND T-BUTYLCYCLOHEXANOLS [J].
CAMPBELL, NC ;
CLARKE, JRP ;
HILL, RR ;
OBERHANS.P ;
PARISH, JH ;
SOUTHAM, RM ;
WHITING, MC .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (03) :349-&
[4]  
DEJTERJUSZYNSKI M, 1963, CARBOHYD RES, V2, P226
[5]  
FLETCHER HG, 1963, METHODS CARBOHYDR CH, V2, P226
[6]   OBSERVATIONS ON SILVER TRIFLUOROMETHANE SULFONATE-PROMOTED SYNTHESES OF 1,2-TRANS-GLYCOSIDES FROM ACYLATED GLYCOSYL BROMIDES [J].
GAREGG, PJ ;
NORBERG, T .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (02) :116-118
[7]   SYNTHESE EINES 1-]4-VERKNUPFTEN DISACCHARIDS AUS ZWEI D-GLUCOSAMIN-EINHEITEN [J].
HEYNS, K ;
PROPP, K ;
HARRISON, R ;
PAULSEN, H .
CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (08) :2655-&
[8]  
JEANLOZ RW, 1962, METHODS CARBOHYDRATE, V1, P221
[9]   THE EFFECT OF HIGH-PRESSURE ON GLYCOSYLATION UNDER HELFERICH CONDITIONS [J].
KOCHETKOV, NK ;
ZHULIN, VM ;
MALYSHEVA, NM ;
KLIMOV, EM ;
MAKAROVA, ZG .
CARBOHYDRATE RESEARCH, 1987, 167 :C8-C10
[10]   THE EFFECT OF HIGH-PRESSURE ON THE STEREOSPECIFICITY OF THE GLYCOSYLATION REACTION [J].
KOCHETKOV, NK ;
ZHULIN, VM ;
KLIMOV, EM ;
MALYSHEVA, NN ;
MAKAROVA, ZG ;
OTT, AY .
CARBOHYDRATE RESEARCH, 1987, 164 :241-254