Stereocontrolled glycosyl transfer reactions with unprotected glycosyl donors

被引:151
作者
Hanessian, S
Lou, BL
机构
[1] Univ Montreal, Dept Chem, Stn Ctr Ville, Montreal, PQ H3C 3J7, Canada
[2] Adv SynTech, Louisville, KY 40299 USA
关键词
D O I
10.1021/cr9903454
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review is given on the methods of O-glycoside synthesis from anomerically activated glycosyl donors in which minimals or no hydroxyl protection is needed. Fisher glycosylation of alcohols is revisited over 100 years later and nature's pathways to glycoside synthesis are emulated albeit with limitations. The concept of remote activation in glycosyl transfer reactions as exemplified by the chemistry of O-unprotected 3-methoxy-2-pyridyloxy (MOP) glycosyl donors is also highlighted.
引用
收藏
页码:4443 / +
页数:22
相关论文
共 220 条
[71]   SYNTHESIS OF (+)-AVERMECTIN-B1A [J].
HANESSIAN, S ;
UGOLINI, A ;
DUBE, D ;
HODGES, PJ ;
ANDRE, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) :2776-2778
[72]  
Hanessian S., UNPUB
[73]  
HANESSIAN S, 1998, Patent No. 5767256
[74]  
HANESSIAN S, 1997, PREPARATIVE CARBOHYD, P381
[75]  
HANESSIAN S, 1980, METHODS CARBOHYDR CH, V8, P243
[76]  
Hanessian S., 1996, PREPARATIVE CARBOHYD
[77]   Dynamic O-linked glycosylation of nuclear and cytoskeletal proteins [J].
Hart, GW .
ANNUAL REVIEW OF BIOCHEMISTRY, 1997, 66 :315-335
[78]   AN EXTREMELY MILD AND STEREOCONTROLLED CONSTRUCTION OF 1,2-TRANS-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON BENZYL-PROTECTED GLYCOPYRANOSYL DIETHYL PHOSPHITES AS GLYCOSYL DONORS [J].
HASHIMOTO, S ;
UMEO, K ;
SANO, A ;
WATANABE, N ;
NAKAJIMA, M ;
IKEGAMI, S .
TETRAHEDRON LETTERS, 1995, 36 (13) :2251-2254
[79]   A RAPID AND EFFICIENT SYNTHESIS OF 1,2-TRANS-BETA-LINKED GLYCOSIDES VIA BENZYL-PROTECTED OR BENZOYL-PROTECTED GLYCOPYRANOSYL PHOSPHATES [J].
HASHIMOTO, S ;
HONDA, T ;
IKEGAMI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :685-687
[80]   GLYCOSYLATION USING GLUCOPYRANOSYL FLUORIDES AND SILICON-BASED CATALYSTS - SOLVENT DEPENDENCY OF THE STEREOSELECTION [J].
HASHIMOTO, S ;
HAYASHI, M ;
NOYORI, R .
TETRAHEDRON LETTERS, 1984, 25 (13) :1379-1382