THE PREPARATION OF C-ARYLGLYCALS - THE PALLADIUM-CATALYZED COUPLING OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-1-(TRIBUTYLSTANNYL)-D-GLUCAL AND ARYL BROMIDES

被引：83

作者：

FRIESEN, RW ^{[1
]}

STURINO, CF ^{[1
]}

机构：

[1] UNIV TORONTO,LASH MILLER CHEM LABS,TORONTO M5S 1A1,ONTARIO,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 09期

关键词：

D O I：

10.1021/jo00296a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed couplings of the protected l-(tributylstannyl)-D-glucal 1 and substituted aryl bromides provide the corresponding C-arylglucals 4-15 and a dimer 16 resulting from the homocoupling of 1. © 1990, American Chemical Society. All rights reserved.

引用

页码：2572 / 2574

页数：3

共 31 条

[1] TOTAL SYNTHESIS OF C-GLYCOSIDE FRAGMENT OF NOGALAMYCIN
BATES, MA
SAMMES, PG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (16) : 896 - 898
[2] STEREOCONTROLLED SYNTHESIS OF C-GLYCOSIDES BY REACTION OF ORGANOCUPRATES WITH PROTECTED 1,2-ANHYDRO SUGARS, AND THEIR TRANSFORMATION INTO 2-DEOXY-C-GLYCOSIDES
BELLOSTA, V
CZERNECKI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) : 199 - 200
[3] C-GLYCOSYL COMPOUNDS .4. SYNTHESIS OF (2-DEOXY-ALPHA-D-GLYC-2-ENOPYRANOSYL)ARENES BY STEREOSPECIFIC CONJUGATE-ADDITION OF ORGANOCOPPER REAGENTS TO PERACETYLATED HEX-1-ENOPYRAN-3-ULOSES
BELLOSTA, V
CZERNECKI, S
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 279 - 288
[4] SYNTHESIS OF C-GLUCOSIDES BY REACTIONS OF GLUCOSYL HALIDES WITH ORGANOCUPRATES
BIHOVSKY, R
SELICK, C
GIUSTI, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) : 4026 - 4031
[5] STUDIES ON C-GLYCOSIDES .13. C-GLUCOSIDES FROM O-GLUCOSYL 3,5-DINITRO BENZOATE
CAI, MS
QIU, DX
[J]. SYNTHETIC COMMUNICATIONS, 1989, 19 (5-6) : 851 - 855
[6] C-GLYCOSIDES FROM PALLADIUM-MEDIATED REACTIONS OF PYRANOID GLYCALS - STEREOCHEMISTRY OF FORMATION OF INTERMEDIATE ORGANOPALLADIUM ADDUCTS AND FACTORS AFFECTING THEIR STABILITY AND DECOMPOSITION
CHENG, JCY
DAVES, GD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) : 3083 - 3090
[7] ARYLATION OF GLYCALS CATALYZED BY PALLADIUM SALTS - NEW SYNTHESIS OF C-GLYCOSIDES
CZERNECKI, S
DECHAVANNE, V
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (03): : 533 - 540
[8] A FULLY SYNTHETIC ROUTE TO THE PAPULACANDINS - STEREOSPECIFIC SPIROACETALIZATION OF A C-1-ARYLATED METHYL GLYCOSIDE
DANISHEFSKY, S
PHILLIPS, G
CIUFOLINI, M
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 317 - 327
[9] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER
DANISHEFSKY, SJ
UANG, BJ
QUALLICH, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) : 1285 - 1293
[10] PALLADIUM-ASSISTED REACTIONS .3. PALLADIUM(0)-ASSISTED SYNTHESIS OF C-GLYCOPYRANOSYL COMPOUNDS
DUNKERTON, LV
EUSKE, JM
SERINO, AJ
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 89 - 107

← 1 2 3 4 →