C-Difluoromethylene-containing, C-trifluoromethyl and C-perfluoroalkyl carbohydrates.: Synthesis by carbohydrate transformation or building block methods

被引:52
作者
Plantier-Royon, R [1 ]
Portella, C [1 ]
机构
[1] Univ Reims, Fac Sci, CNRS UMR 6519, Lab React Select & Applicat, F-51687 Reims, France
关键词
C-difluoromethylene carbohydrates; C-trifluoromethyl carbohydrates; C-perfluoroalkyl carbohydrates; fluorinated synthons;
D O I
10.1016/S0008-6215(00)00034-3
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 synthetic methods for preparing carbohydrates bearing a C-branched substituent of the type CF2-Y, with Y = F, Y = CnF2n+1 or Y = a carbon-attached or heteroatom-attached nonfluorinated residues, are reviewed. Both direct introduction of C-branched fluorinated substituents (direct trifluoromethylation, perfluoroalkylation or difluoromethylenation) and building block methods from fluorinated synthons are considered. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:119 / 146
页数:28
相关论文
共 98 条
[1]  
Arnone A, 1998, SYNTHESIS-STUTTGART, P1511
[2]   SYNTHESIS OF TRIFLUOROMETHYL ANALOG OF L-FUCOSE AND 6-DEOXY-D-ALTROSE [J].
BANSAL, RC ;
DEAN, B ;
HAKOMORI, S ;
TOYOKUNI, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) :796-798
[3]   Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases [J].
Behr, JB ;
Evina, CM ;
Phung, N ;
Guillerm, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1597-1599
[4]  
BERBER H, UNPUB
[5]   FLUORINATED KETENE DITHIOACETALS .3. A RADICAL ENTRY TO ALPHA-PERFLUOROALKYL KETENE DITHIOACETALS - APPLICATION TO SUGAR-DERIVATIVES [J].
BERGERON, S ;
BRIGAUD, T ;
FOULARD, G ;
PLANTIERROYON, R ;
PORTELLA, C .
TETRAHEDRON LETTERS, 1994, 35 (13) :1985-1988
[6]   SYNTHESIS OF THE (ALPHA,ALPHA-DIFLUOROALKYL)PHOSPHONATE ANALOG OF PHOSPHOSERINE [J].
BERKOWITZ, DB ;
SHEN, QR ;
MAENG, JH .
TETRAHEDRON LETTERS, 1994, 35 (35) :6445-6448
[7]   DIALLYL (LITHIODIFLUOROMETHYL)PHOSPHONATE - A NEW REAGENT FOR THE INTRODUCTION OF THE (DIFLUOROMETHYLENE)PHOSPHONATE FUNCTIONALITY [J].
BERKOWITZ, DB ;
SLOSS, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7047-7050
[8]   SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES [J].
BLACKBURN, GM ;
KENT, DE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06) :913-917
[9]  
BLACKBURN GM, 1985, J CHEM RES-S, P92
[10]   ISOPOLAR VS ISOSTERIC PHOSPHONATE ANALOGS OF NUCLEOTIDES [J].
BLACKBURN, GM ;
ECKSTEIN, F ;
KENT, DE ;
PERREE, TD .
NUCLEOSIDES & NUCLEOTIDES, 1985, 4 (1-2) :165-167