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
[1]   Efficient intramolecular β-mannoside formation using m-xylylene and isophthaloyl derivatives as rigid spacers [J].
Abdel-Rahman, AAH ;
El Ashry, EH ;
Schmidt, RR .
CARBOHYDRATE RESEARCH, 2002, 337 (03) :195-206
[2]  
Abdel-Rahman AAH, 2002, ANGEW CHEM INT EDIT, V41, P2972, DOI 10.1002/1521-3773(20020816)41:16<2972::AID-ANIE2972>3.0.CO
[3]  
2-4
[4]  
ABDELRAHMAN AAH, UNPUB
[5]   PREPARATION OF DISACCHARIDES HAVING A BETA-D-MANNOPYRANOSYL GROUP FROM N-PHTHALOYLLACTOSAMINE DERIVATIVES BY DOUBLE OR TRIPLE SN2 SUBSTITUTION [J].
ALAIS, J ;
DAVID, S .
CARBOHYDRATE RESEARCH, 1990, 201 (01) :69-77
[6]   Protection of hydroxy groups with diphenylmethyl and 9-fluorenyl trichloroacetimidates - Effect on anomeric stereocontrol [J].
Ali, IAI ;
El Ashr, ESH ;
Schmidt, RR .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4121-4131
[7]  
ANDERSSON F, 1989, ACS SYM SER, V386, P117
[8]  
ANDRESSON F, 1990, TETRAHEDRON LETT, V86, P3919
[9]   AMINO-SUGARS .123. THE SYNTHESIS OF O-BETA-D-MANNOPYRANOSYL-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE .2. [J].
AUGE, C ;
WARREN, CD ;
JEANLOZ, RW ;
KISO, M ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1980, 82 (01) :85-95
[10]   A SYNTHESIS OF METHYL 3-O-(BETA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE FROM SULFONATE INTERMEDIATES [J].
AWAD, LF ;
ELASHRY, ESH ;
SCHUERCH, C .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (05) :1587-1592