C-GLYCOSIDES - PD/CU CO-CATALYZED THIOCARBOXYLATION OF STANNYL GLUCOPYRANOSIDES

被引:35
作者
BELOSLUDTSEV, YY
BHATT, RK
FLACK, JR
机构
[1] UNIV TEXAS,SW MED CTR,DEPT MOLEC GENET,DALLAS,TX 75235
[2] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
关键词
D O I
10.1016/0040-4039(95)01183-I
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereospecific Pd/Cu co-catalyzed cross-couplings of tributylstannyl glucopyranosides with thiono- and thiolchloroformates afford good to excellent yields of C-glucosyl thiocarboxylates, versatile precursors for more complex C-glucoside homologs.
引用
收藏
页码:5881 / 5882
页数:2
相关论文
共 13 条
[1]   STANNYLMETALLATION OF CONJUGATED ENYNES [J].
AKSELA, R ;
OEHLSCHLAGER, AC .
TETRAHEDRON, 1991, 47 (07) :1163-1176
[2]   SYNTHESIS OF C-GLUCOSIDES BY REACTIONS OF GLUCOSYL HALIDES WITH ORGANOCUPRATES [J].
BIHOVSKY, R ;
SELICK, C ;
GIUSTI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4026-4031
[3]   CATALYTIC SILOXYMETHYLATION OF GLYCOSIDES BY THE HSIR3/CO/CO2(CO)8 REACTION - A NEW ENTRY TO C-GLYCOSYL COMPOUNDS [J].
CHATANI, N ;
IKEDA, T ;
SANO, T ;
SONODA, N ;
KUROSAWA, H ;
KAWASAKI, Y ;
MURAI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3387-3389
[4]   ORGANO-TRANSITION-METAL-BASED APPROACH TO THE SYNTHESIS OF C-GLYCOSIDES [J].
DESHONG, P ;
SLOUGH, GA ;
ELANGO, V ;
TRAINOR, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7788-7790
[5]   FURAN-BASED SYNTHESIS OF C-GLYCOSYL CARBOXYLATES [J].
DONDONI, A ;
MARRA, A ;
SCHERRMANN, MC .
TETRAHEDRON LETTERS, 1993, 34 (45) :7323-7326
[6]   ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].
FARINA, V ;
KAPADIA, S ;
KRISHNAN, B ;
WANG, CJ ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911
[7]   FACILE REDUCTION OF ETHYL THIOL ESTERS TO ALDEHYDES - APPLICATION TO A TOTAL SYNTHESIS OF (+)-NEOTHRAMYCIN-A METHYL-ETHER [J].
FUKUYAMA, T ;
LIN, SC ;
LI, LP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7050-7051
[8]   ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].
HALCOMB, RL ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666
[9]  
JARAMILLO C, 1994, SYNTHESIS-STUTTGART, P1
[10]  
KUROBOSHI M, 1994, SYNLETT, P251