Glycoside Bond Formation via Acid-Base Catalysis

被引:71
作者
Kumar, Amit [1 ]
Kumar, Vipin [1 ]
Dere, Ravindra T. [1 ]
Schmidt, Richard R. [1 ]
机构
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
关键词
SOLID-PHASE SYNTHESIS; O-GLYCOSYL; HEXOPYRANOSIDES; DISACCHARIDE; MECHANISM;
D O I
10.1021/ol201231v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acid-base catalyzed glycosyl donor and then glycosyl acceptor activation with phenylboron difluoride or diphenylboron fluoride permits hydrogen bond mediated Intramolecular S(N)2-type glycosidation In generally high anomeric selectivity.
引用
收藏
页码:3612 / 3615
页数:4
相关论文
共 45 条
[1]   REACTIONS OF RELEVANCE TO THE CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .13. A NOVEL SYNTHESIS OF BENZYL ETHERS [J].
BARRETT, AGM ;
READ, RW ;
BARTON, DHR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2184-2190
[2]   GLYCOSYLIDENE CARBENES - A NEW APPROACH TO GLYCOSIDE SYNTHESIS .1. PREPARATION OF GLYCOSYLIDENE-DERIVED DIAZIRIDINES AND DIAZIRINES [J].
BRINER, K ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1989, 72 (06) :1371-1382
[3]   2,3-anhydrosugars in glycoside bond synthesis. NMR and computational investigations into the mechanism of glycosylations with 2,3-anhydrofuranosyl glycosyl sulfoxides [J].
Callam, CS ;
Gadikota, RR ;
Krein, DM ;
Lowary, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) :13112-13119
[4]   First synthesis of anomeric sulfimides - efficient glycosyl donors [J].
Cassel, S ;
Plessis, I ;
Wessel, HP ;
Rollin, P .
TETRAHEDRON LETTERS, 1998, 39 (44) :8097-8100
[5]   Catalytic and stereoselective glycosylation with glucosyl thioformimidates [J].
Chiba, H ;
Funasaka, S ;
Mukaiyama, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (08) :1629-1644
[6]   Mechanism of a Chemical Glycosylation Reaction [J].
Crich, David .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (08) :1144-1153
[7]   Recent developments in oligosaccharide synthesis [J].
Davis, BG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2137-2160
[8]  
Demchenko A. V., 2008, HDB CHEM GLYCOSYLATI
[9]  
DERE RT, J ORG CHEM UNPUB
[10]   USE OF 1-ORTHO-TOSYL-D-GLUCOPYRANOSE DERIVATIVES IN ALPHA-D-GLUCOSIDE SYNTHESIS [J].
EBY, R ;
SCHUERCH, C .
CARBOHYDRATE RESEARCH, 1974, 34 (01) :79-90