REDUCTIVE CLEAVAGE AS A ROUTE TO CARBOHYDRATE ENOLATES - APPLICATIONS TO THE SYNTHESIS OF C-LINKED DISACCHARIDES

被引:27
作者
BINCH, HM
GRIFFIN, AM
SCHWIDETZKY, S
RAMSAY, MVJ
GALLAGHER, T
LICHTENTHALER, FW
机构
[1] UNIV BRISTOL,SCH CHEM,BRISTOL BS8 1TS,AVON,ENGLAND
[2] TH DARMSTADT,INST ORGAN CHEM,D-64287 DARMSTADT,GERMANY
[3] GLAXO GRP RES LTD,RES & DEV,DEPT MED CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1039/c39950000967
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The carbohydrate-derived alpha-bromo ketones 4 and 5 undergo reductive cleavage using either Zn-Cu or CeCl3-Nal and the resulting enolates are trapped by carbohydrate-based aldehydes 6, 7 and 14 to give C-disaccharide derivatives.
引用
收藏
页码:967 / 968
页数:2
相关论文
共 29 条
[1]   DESOXYNITRO SUGARS .3. SYNTHESIS OF KETOSES BY CHAIN ELONGATION OF 1-DEOXY-1-NITROALDOSES - NUCLEOPHILIC ADDITIONS AND SOLVOLYSIS OF NITRO ETHERS [J].
AEBISCHER, B ;
BIERI, JH ;
PREWO, R ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1982, 65 (07) :2251-2272
[2]   SYNTHESIS OF BIS-GAMMA-LACTONES FROM DIACETONE GLUCOSE .4. OPTICALLY-ACTIVE AVENACIOLIDE AND ISOAVENACIOLIDE [J].
ANDERSON, RC ;
FRASERREID, B .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4781-4786
[3]   CHROMIUM TRIOXIDE-DIPYRIDINE COMPLEX AS AN OXIDANT FOR PARTIALLY PROTECTED SUGARS - PREPARATION OF ALDEHYDO AND CERTAIN KETO SUGAR DERIVATIVES [J].
ARRICK, RE ;
BAKER, DC ;
HORTON, D .
CARBOHYDRATE RESEARCH, 1973, 26 (02) :441-447
[4]   PREPARATION AND REDUCTIVE LITHIATION OF 2-DEOXY-D-GLUCOPYRANOSYL PHENYLSULFONES - A HIGHLY STEREOSELECTIVE ROUTE TO C-GLYCOSIDES [J].
BEAU, JM ;
SINAY, P .
TETRAHEDRON LETTERS, 1985, 26 (50) :6185-6188
[5]   CHEMISTRY OF THE HERBICIDINS - REACTIVITY OF SILYL ENOL ETHERS DERIVED FROM SIMPLE AND CARBOHYDRATE-BASED TETRAHYDROPYRANS [J].
COX, PJ ;
GRIFFIN, AM ;
NEWCOMBE, NJ ;
LISTER, S ;
RAMSAY, MVJ ;
ALKER, D ;
GALLAGHER, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11) :1443-1447
[6]  
DEPOUILLY P, 1993, B SOC CHIM FR, V130, P256
[7]   REGIOSPECIFIC SYNTHESIS OF 2-PHENYLPYRANO[3,4-B]PYRANONES (OXAFLAVONE DERIVATIVES) WITH TETRAHYDRO-3-PYRANONE [J].
EIDEN, F ;
WANNER, KT .
ARCHIV DER PHARMAZIE, 1985, 318 (03) :207-209
[8]   PREPARATION AND TRANSMETALATION OF A TRIPHENYLSTANNYL BETA-D-GLUCOPYRANOSIDE - A HIGHLY STEREOSELECTIVE ROUTE TO BETA-D-C-GLYCOSIDES VIA GLYCOSYL DIANIONS [J].
FREY, O ;
HOFFMANN, M ;
WITTMANN, V ;
KESSLER, H ;
UHLMANN, P ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1994, 77 (07) :2060-2069
[9]   REACTION OF ALPHA-HALOGENO KETONES WITH CARBONYL-COMPOUNDS PROMOTED BY CEL3, CECL3-NAL, OR CECL3-SNCL2 [J].
FUKUZAWA, S ;
TSURUTA, T ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1473-1477
[10]   CARBON-CARBON BOND FORMATION BETWEEN ALPHA-HALOGENOKETONES AND ALDEHYDES PROMOTED BY CERIUM(III) IODIDE OR CERIUM(III) CHLORIDE-SODIUM IODIDE [J].
FUKUZAWA, S ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (12) :777-778