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
[91]  
Yamazaki T, 1996, ACS SYM SER, V639, P105
[92]   MODIFIED PREPARATION METHOD OF TRIFLUOROMETHYLATED PROPARGYLIC ALCOHOLS AND ITS APPLICATION TO CHIRAL 2,6-DIDEOXY-6,6,6-TRIFLUOROSUGARS [J].
YAMAZAKI, T ;
MIZUTANI, K ;
KITAZUME, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6046-6056
[93]   STEREOSELECTIVE PREPARATION OF OPTICALLY-ACTIVE 6-DEOXY-6,6,6-TRIFLUOROHEXOPYRANOSES [J].
YAMAZAKI, T ;
MIZUTANI, K ;
KITAZUME, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (09) :734-745
[94]   PREPARATION OF 6-DEOXY-6,6,6-TRIFLUORO-D-MANNOSE AND D-ALLOSE FROM ENZYMATICALLY RESOLVED 2-BUTENOLIDES [J].
YAMAZAKI, T ;
MIZUTANI, K ;
KITAZUME, T .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :1059-1062
[95]   DEVELOPMENT OF A NOVEL PATHWAY TO ACCESS 6-DEOXY-6,6,6-TRIFLUOROSUGARS VIA 1,2-MIGRATION OF A TERT-BUTYLDIMETHYLSILYL GROUP [J].
YAMAZAKI, T ;
MIZUTANI, K ;
KITAZUME, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4346-4359
[96]   Highly stereoselective route to aldol products incorporating fluorine-containing methyl groups starting from a single D-glucose-derived intermediate [J].
Yamazaki, T ;
Hiraoka, S ;
Kitazume, T .
TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1157-1160
[97]  
Zur C, 1998, EUR J ORG CHEM, V1998, P531, DOI 10.1002/(SICI)1099-0690(199803)1998:3<531::AID-EJOC531>3.0.CO
[98]  
2-E