Strategies of synthetic methodologies for constructing β-mannosidic linkage

被引:46
作者
El Ashry, ESH [1 ]
Rashed, N
Ibrahim, ESI
机构
[1] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt
[2] Suez Canal Univ, Ismailia, Egypt
关键词
glycosyl acceptors; mannosyl donor; aglycon delivery; epimerization; beta-mannopyranosides; stereoselective mannosidation; 1,2-cis-mannosides; benzylsulfonyl;
D O I
10.2174/1570179053545378
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The various synthetic methodologies for constructing the beta-mannosidic bonds have been reviewed. Different strategies are covered such as inter and intramolecular glycosidation methods as well as epimerization of beta-glucosides, reductive cleavage of anomeric orthoesters, radical anomeric inversion, enzymatic synthesis and mannosides from non-carbohydrate.
引用
收藏
页码:175 / 213
页数:39
相关论文
共 185 条
[11]  
AWAD LF, 1984, THESIS ALEXANDRIA U
[12]   SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY [J].
BARRESI, F ;
HINDSGAUL, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9376-9377
[13]  
BARRESI F, 1992, SYNLETT, P759
[14]   THE SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY - SCOPE AND LIMITATIONS OF THE EXISTING METHODOLOGY [J].
BARRESI, F ;
HINDSGAUL, O .
CANADIAN JOURNAL OF CHEMISTRY, 1994, 72 (06) :1447-1465
[15]  
BARRESI F, 1996, MODERN METHODS CARBO, V11, P251
[16]   SYNTHESIS OF 4-O-BETA-D-MANNOPYRANOSYL-L-RHAMNOPYRANOSE [J].
BEBAULT, GM ;
DUTTON, GGS .
CARBOHYDRATE RESEARCH, 1974, 37 (02) :309-319
[17]   PRACTICAL SYNTHESIS OF O-BETA-D-MANNOPYRANOSYL O-ALPHA-D-MANNOPYRANOSYL AND O-BETA-D-GLUCOPYRANOSYL-(1-]4)-O-ALPHA-D-RHAMNOPYRANOSYL-(1-]3)-D-GALACTOSES [J].
BETANELI, VI ;
OVCHINNIKOV, MV ;
BACKINOWSKY, LV ;
KOCHETKOV, NK .
CARBOHYDRATE RESEARCH, 1980, 84 (02) :211-224
[18]   A DIVERGENT DENOVO SYNTHESIS OF CARBOHYDRATES BASED ON AN ACCELERATED INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 1-OXA-1,3-BUTADIENES [J].
BOGER, DL ;
ROBARGE, KD .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5793-5796
[19]  
Boons GJ, 1997, SYNLETT, P809
[20]   BENZYLATED ORTHOESTERS IN GLYCOSIDE SYNTHESIS - SYNTHESIS OF ALPHA-D-GLUCOPYRANOSIDES AND BETA-D-MANNOPYRANOSIDES [J].
BOREN, HB ;
EKBORG, G ;
EKLIND, K ;
GAREGG, PJ ;
PILOTTI, A ;
SWAHN, CG .
ACTA CHEMICA SCANDINAVICA, 1973, 27 (07) :2639-2644