Stereospecific synthesis of β-D-allopyrano sides by dihydroxylation of β-D-erythro-2,3-dideoxyhex-2-enopyranosides

被引:19
作者
Murphy, PV [1 ]
O'Brien, JL
Smith, AB
机构
[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Conway Inst Biomol & Biomed Res, Dublin 4, Ireland
[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
stereospecific synthesis; beta-D-allopyranoside; dihydroxylation; beta-D-erythro-2,3-Dideoxyhex-2-enopyrano sides; inversion of configuration;
D O I
10.1016/S0008-6215(01)00181-1
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 synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:327 / 335
页数:9
相关论文
共 26 条
[1]   SYNTHESIS OF 2,4-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOSYL NUCLEOSIDES [J].
AUGUSTYNS, K ;
ROZENSKI, J ;
VANAERSCHOT, A ;
JANSSEN, G ;
HERDEWIJN, P .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2977-2982
[2]   SYNTHESIS OF 2-AMINO-2-DEOXY AND 3-AMINO-3-DEOXY-ALPHA-D-MANNOPYRANOSYL ALPHA-D-MANNOPYRANOSIDE BY SEQUENTIAL OSMYLATIONS OF A DIENIC DISACCHARIDE [J].
BAER, HH ;
SIEMSEN, L .
CARBOHYDRATE RESEARCH, 1986, 146 (01) :63-72
[3]   Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis [J].
Cook, BN ;
Bhakta, S ;
Biegel, T ;
Bowman, KG ;
Armstrong, JI ;
Hemmerich, S ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8612-8622
[4]  
CRIDLEY JJ, 1998, TETRAHEDRON, V54, P14925
[5]   Synthesis of 2,3-unsaturated 4-amino sugars and cyclohexyl 2,3-di-O-acetyl-4,6-di-O-methyl-α-D-manno- pyranoside from cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside [J].
de Brito, TMB ;
da Silva, LP ;
Siqueira, VL ;
Srivastava, RM .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1999, 18 (06) :609-616
[6]   INVOLVEMENT OF THE GLUCOSE MOIETY IN THE MOLECULAR RECOGNITION OF METHYL BETA-LACTOSIDE BY RICIN - SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND BINDING-STUDIES OF DIFFERENT DERIVATIVES AT THE C-3 REGION [J].
FERNANDEZ, P ;
JIMENEZBARBERO, J ;
MARTINLOMAS, M ;
SOLIS, D ;
DIAZMAURINO, T .
CARBOHYDRATE RESEARCH, 1994, 256 (02) :223-244
[7]   ON THE USE OF THE HALOETHERIFICATION METHOD TO SYNTHESIZE FULLY FUNCTIONALIZED DISACCHARIDES [J].
FRIESEN, RW ;
DANISHEFSKY, SJ .
TETRAHEDRON, 1990, 46 (01) :103-112
[8]  
GAREGG PJ, 1979, SYNTHESIS-STUTTGART, P469
[9]   Recent advances in the construction of β-D-mannose and β-D-mannosamine linkages [J].
Gridley, JJ ;
Osborn, HMI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10) :1471-1491
[10]   Syntheses of D- and L-mannose, gulose, and talose via diastereoselective and enantioselective dihydroxylation reactions [J].
Harris, JM ;
Keranen, MD ;
O'Doherty, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2982-2983