New Developments in the Synthesis of Deoxy- and Branched-chain Sugars

被引:10
作者
Bielski, Roman [1 ]
Witczak, Zbigniew J. [1 ]
机构
[1] Wilkes Univ, Nesbitt Sch Pharm, Dept Pharmaceut Sci, Wilkes Barre, PA 18707 USA
关键词
Deoxysugars; branched-chain sugars; chemical synthesis; enzymatic synthesis; O-ANTIGEN POLYSACCHARIDE; DE-NOVO SYNTHESIS; C BOND FORMATION; HELICOBACTER-PYLORI; MICHAEL ADDITION; REPEATING UNIT; GENERAL-ROUTE; ACERIC ACID; DIHYDROXYLATION; FRAGMENTATION;
D O I
10.2174/1385272819666140527232605
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The existing methodologies for the synthesis of 6-, 5-, 4-, 3-, 2-deoxysugars and functionalized branched-chain sugars at C-6, C-5, C-4, C-3, C-2 positions were compiled and reviewed.
引用
收藏
页码:1897 / 1912
页数:16
相关论文
共 66 条
[1]   Influence of nonionic branched-chain alkyl glycosides on a model nano-emulsion for drug delivery systems [J].
Ahmad, Noraini ;
Ramsch, Roland ;
Llinas, Meritxell ;
Solans, Conxita ;
Hashim, Rauzah ;
Tajuddin, Hairul Anuar .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2014, 115 :267-274
[2]   De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate [J].
Ahmed, MM ;
Berry, BP ;
Hunter, TJ ;
Tomcik, DJ ;
O'Doherty, GA .
ORGANIC LETTERS, 2005, 7 (04) :745-748
[3]  
Al-Mouamin T.M., 2012, BASIC ED COLL MAGAZI, V1, P38
[4]   The Wittig-cyclization procedure:: acid promoted intramolecular formation of 3-C-branched-chain 3,6-anhydro furano sugars via 2′-oxopropylene derivatives [J].
Ay, Kadir ;
Cetin, Fatma ;
Yuceer, Levent .
CARBOHYDRATE RESEARCH, 2007, 342 (08) :1091-1095
[5]   α-Selective Organocatalytic Synthesis of 2-Deoxygalactosides [J].
Balmond, Edward I. ;
Coe, Diane M. ;
Galan, M. Carmen ;
McGarrigle, Eoghan M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9152-9155
[6]   Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars [J].
Best, Daniel ;
Jenkinson, Sarah F. ;
Saville, A. Waldo ;
Alonzi, Dominic S. ;
Wormald, Mark R. ;
Butters, Terry D. ;
Norez, Caroline ;
Becq, Frederic ;
Bleriot, Yves ;
Adachi, Isao ;
Kato, Atsushi ;
Fleet, George W. J. .
TETRAHEDRON LETTERS, 2010, 51 (32) :4170-4174
[7]   Platinum-catalyzed ring opening of 1,2-cyclopropanated sugars with O-nucleophiles.: Convenient synthesis of 2-C-branched carbohydrates [J].
Beyer, J ;
Skaanderup, PR ;
Madsen, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (40) :9575-9583
[8]   Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection [J].
Booth, K. Victoria ;
Jenkinson, Sarah F. ;
Best, Daniel ;
Fernandez Nieto, Fernando ;
Estevez, Ramon J. ;
Wormald, Mark R. ;
Weymouth-Wilson, Alexander C. ;
Fleet, George W. J. .
TETRAHEDRON LETTERS, 2009, 50 (36) :5088-5093
[9]   Oxidative cleavage of 3-alkoxy-2,5-dihydrofurans and its application to the de novo synthesis of rare monosaccharides as exemplified by L-cymarose [J].
Brasholz, Malte ;
Reissig, Hans-Ulrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1634-1637
[10]   De Novo Synthesis of L-Colitose and L-Rhodinose Building Blocks [J].
Calin, Oliviana ;
Pragani, Rajan ;
Seeberger, Peter H. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :870-877