A SIMPLE STEREOSPECIFIC ROUTE TO 5-C-ALKOXY-D-GALACTOPYRANOSIDES AND TO L-ARABINO-HEXOS-5-ULOSES

被引:14
作者
BARILI, PL
BERTI, G
CATELANI, G
DANDREA, F
机构
[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY
[2] UNIV FERRARA,DIPARTIMENTO SCI FARMACEUT,I-44100 FERRARA,ITALY
关键词
D O I
10.1016/S0040-4039(00)92130-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-C-alkoxy-beta-D-galactopyranosides, which are easily convertible into L-arabino-hexos-5-uloses, can be prepared from beta-D-galactopyranosides via peroxyacid oxidation in an alcoholic solvent of intermediate 4-deoxy-alpha-L-threo-hex-4-enopyranosides.
引用
收藏
页码:959 / 962
页数:4
相关论文
共 7 条
[1]   A FACILE CONVERSION OF 3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDES INTO 4-DEOXY-ALPHA-L-THREO-HEX-4-ENOPYRANOSIDE AND L-ARABINO-HEXOS-5-ULOSE DERIVATIVES [J].
BARILI, PL ;
BERTI, G ;
CATELANI, G ;
COLONNA, F ;
DANDREA, F .
CARBOHYDRATE RESEARCH, 1989, 190 (01) :13-21
[2]   META-CHLOROPERBENZOIC ACID AS A SELECTIVE REAGENT FOR THE REMOVAL OF O-PROPENYL GROUPS - ITS USE IN THE SYNTHESIS OF SOME D-GALACTOPYRANOSIDE AND 4-DEOXY-L-THREO-4-HEXENOPYRANOSIDE DERIVATIVES [J].
BARILI, PL ;
BERTI, G ;
BERTOZZI, D ;
CATELANI, G ;
COLONNA, F ;
CORSETTI, T ;
DANDREA, F .
TETRAHEDRON, 1990, 46 (15) :5365-5376
[3]  
BERTI G, 1972, TOP STEREOCHEM, V7, P130
[4]   ASSIGNMENT OF RING SIZE IN ISOPROPYLIDENE ACETALS BY C-13 NMR-SPECTROSCOPY [J].
BUCHANAN, JG ;
EDGAR, AR ;
RAWSON, DI ;
SHAHIDI, P ;
WIGHTMAN, RH .
CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :75-86
[5]   PHOTO-BROMINATION OF CARBOHYDRATE-DERIVATIVES .3. C-5 BROMINATION OF PENTA-O-BENZOYL-ALPHA-AND-BETA-D-GLUCOPYRANOSE - A ROUTE TO D-XYLO-HEXOS-5-ULOSE DERIVATIVES AND ALPHA-L-IDOPYRANOSIDES [J].
FERRIER, RJ ;
TYLER, PC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07) :1528-1534
[6]   CYCLIZATION OF D-XYLO-HEXOS-5-ULOSE A CHEMICAL SYNTHESIS OF SCYLLO-INOSITOLS AND MYO-INOSITOLS FROM D-GLUCOSE [J].
KIELY, DE ;
FLETCHER, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (05) :1386-&
[7]   SYNTHESIS OF 9-(3-DEOXY-3-FLUORO-BETA-D-RIBOFURANOSYL)GUANINE, A NEW POTENT ANTIVIRAL AGENT [J].
PUECH, F ;
GOSSELIN, G ;
IMBACH, JL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :955-957