Synthesis of homochiral 2-C-perfluoroalkyl substituted D- and L-riboses

被引:5
作者
Eilitz, U
Böttcher, C
Hennig, L
Haas, A
Boyer, C
Burger, Y
机构
[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany
[2] Ruhr Univ Bochum, D-44780 Bochum, Germany
关键词
stereoselective fluoroalkylation reactions; 2-C-heptafluoropropyl D-ribose; 2-C-nonafluorobutyl L-ribose;
D O I
10.1016/S0022-1139(02)00042-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Homochiral 2-C-perfluoroalkyl substituted D- and L-riboses were synthesized via Barbier, Grignard and Ruppert type reactions. The influence of the size of the perfluoroalkyl groups, attached to C-2, on the furanose/pyranose as well as on the alpha-furanose/beta-furanose and alpha-pyranose/beta-pyranose ratio in solution was studied. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:149 / 154
页数:6
相关论文
共 35 条
[21]   Liquid crystals based on fluorinated carbohydrates [J].
Miethchen, R ;
Hein, M .
CARBOHYDRATE RESEARCH, 2000, 327 (1-2) :169-183
[22]  
MURAI Y, 1992, HETEROCYCLES, V33, P391
[23]  
Ojima I., 1996, ACS S SERIES, V639
[24]  
Peters D, 1998, SYNTHESIS-STUTTGART, P1033
[25]   SYNTHESIS OF L-2-SPIROCYCLOPROPYL-2-DEOXYARABINOSE [J].
PETTER, RC ;
POWERS, DG .
TETRAHEDRON LETTERS, 1989, 30 (06) :659-662
[26]   C-Difluoromethylene-containing, C-trifluoromethyl and C-perfluoroalkyl carbohydrates.: Synthesis by carbohydrate transformation or building block methods [J].
Plantier-Royon, R ;
Portella, C .
CARBOHYDRATE RESEARCH, 2000, 327 (1-2) :119-146
[27]   SYNTHESIS OF SOME 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES DERIVED FROM MODIFIED PYRIMIDINE-BASES [J].
REESE, CB ;
VARAPRASAD, CVNS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (02) :189-195
[28]   Carbohydrate- and related polyol-derived fluorosurfactants: an update [J].
Riess, JG ;
Greiner, J .
CARBOHYDRATE RESEARCH, 2000, 327 (1-2) :147-168
[29]  
SANDERSON PN, 1997, CARBOHYD RES, V119, P11746
[30]  
SCHMIT C, 1994, SYNLETT, P238