TOTAL SYNTHESIS OF UNDECULOFURANOSIDURONIC ACID-DERIVATIVES RELATED TO HERBICIDINS

被引:17
作者
EMERY, F [1 ]
VOGEL, P [1 ]
机构
[1] UNIV LAUSANNE,CHIM SECT,2 RUE BARRE,CH-1005 LAUSANNE,SWITZERLAND
关键词
LONG-CHAIN; BRANCHED CARBOHYDRATES; METHYL 6,10-ANHYDRO-5-DEOXY-BETA-DL-LYXO-LD-TALO-7-UNDECULOFURANURONATE; C-GLYCOSIDES;
D O I
10.1016/S0040-4039(00)60529-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of methyl 5-deoxy-2,3-O-isopropylidene-beta-DL-ribo-hexodialdo-1,4-furanoside with the enolate of 5-deoxy-2-O-mesyl-3-O-methoxymethyl-beta-DL-arabino-hexo-furanurono-6,1-lactone gave a branched dodecose derivative which was converted into 6,10-anhydro-5-deoxy-DL-lyxo-LD-talo-7-undeculofuranuronic acid derivatives.
引用
收藏
页码:4209 / 4212
页数:4
相关论文
共 40 条
[1]   SYNTHESIS OF ALPHA-(1-]2)-, ALPHA-(1-]3)-, ALPHA-(1-]4)-, AND ALPHA-(1-]5)-C-LINKED DISACCHARIDES THROUGH 2,3,4,6-TETRA-O-ACETYLGLUCOPYRANOSYL RADICAL ADDITIONS TO 3-METHYLIDENE-7-OXABICYCLO[2.2.1]HEPTAN-2-ONE DERIVATIVES [J].
BIMWALA, RM ;
VOGEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2076-2083
[2]  
Buchanan J. G., 1982, TOPICS ANTIBIOTIC CH, V6, P229
[3]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[4]   ASCENT OF THE ALDOSE SERIES BY 4 CARBON-ATOMS - TOTAL SYNTHESIS OF D-GLYCERO-D-TALO-L-TALO-UNDECOSE PENTAACETONIDE [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2135-2139
[5]  
CHEN Y, 1992, TETRAHEDRON LETT, V48, P4917
[6]  
DAI X, 1989, FAMING ZHUANLI SHENQ, V111
[7]   A FULLY SYNTHETIC ROUTE TO TUNICAMINYLURACIL [J].
DANISHEFSKY, S ;
BARBACHYN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7761-7762
[8]   TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].
DANISHEFSKY, SJ ;
DENINNO, MP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23
[9]   FULLY SYNTHETIC STEREOSELECTIVE ROUTES TO THE DIFFERENTIALLY PROTECTED SUBUNITS OF THE TUNICAMYCINS [J].
DANISHEFSKY, SJ ;
DENINNO, SL ;
CHEN, S ;
BOISVERT, L ;
BARBACHYN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5810-5818
[10]  
DANISHEFSKY SJ, 1985, J AM CHEM SOC, V107, P7763