PREPARATION OF C-ARYL GLUCALS VIA THE PALLADIUM-CATALYZED COUPLING OF METALATED AROMATICS WITH 1-IODO-3,4,6-TRI-O-(TRIISOPROPYLSILYL)-D-GLUCAL

被引：64

作者：

FRIESEN, RW

LOO, RW

机构：

[1] Lash Miller Chemical Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 1A1

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 16期

关键词：

D O I：

10.1021/jo00016a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of the novel iodo glucal 5 from 3,4,6-tri-O-(triisopropylsilyl)-D-glucal (4), via a two-step procedure involving C1 stannylation and subsequent tiniodine exchange, is described. The palladium-catalyzed coupling of 5 with a variety of metalated aromatics provides a facile and high yielding entry into C-aryl glucals, compounds that have been demonstrated to be useful precursors for the synthesis of C-aryl glycosides.

引用

页码：4821 / 4823

页数：3

共 19 条

[1] THE CROSS-COUPLING REACTIONS OF ORGANIC HALIDES WITH ORGANIC DERIVATIVES OF TIN, MERCURY AND COPPER CATALYZED BY PALLADIUM [J].

BELETSKAYA, IP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) :551-564

[2] CYCLIC VINYL ETHER CARBANIONS .2. PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL-COMPOUNDS [J].

BOECKMAN, RK ;

BRUZA, KJ .

TETRAHEDRON, 1981, 37 (23) :3997-4006

[3]

DANG HP, 1978, TETRAHEDRON LETT, P191

[4] STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES [J].

DANISHEFSKY, SJ ;

DENINNO, MP ;

CHEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3929-3940

[5] ARYLATION OF 1-TRIBUTYLSTANNYL GLYCALS CATALYZED BY PALLADIUM - A SYNTHETIC ROUTE TO THE BASIC SKELETON OF THE PAPULACANDINS AND CHAETIACANDIN [J].

DUBOIS, E ;

BEAU, JM .

TETRAHEDRON LETTERS, 1990, 31 (36) :5165-5168

[6] FORMATION OF C-GLYCOSIDES BY A PALLADIUM-CATALYZED COUPLING REACTION OF TRIBUTYLSTANNYL GLYCALS WITH ORGANIC HALIDES [J].

DUBOIS, E ;

BEAU, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) :1191-1192

[7] STEREOSELECTIVE OXIDATIVE SPIROKETALIZATION OF A C-ARYLGLUCAL DERIVED FROM PALLADIUM-CATALYZED COUPLING - SYNTHESIS OF THE C-ARYLGLUCOSIDE SPIROKETAL NUCLEUS OF THE PAPULACANDINS [J].

FRIESEN, RW ;

STURINO, CF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5808-5810

[8] OBSERVATION OF ALPHA-SILYL CARBANIONS IN THE METALATION OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL [J].

FRIESEN, RW ;

STURINO, CF ;

DALJEET, AK ;

KOLACZEWSKA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1944-1947

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

FRIESEN, RW ;

STURINO, CF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2572-2574

[10] HYDROBORATION OF C-ARYLGLUCALS - SYNTHESIS OF THE BETA-C-ARYLGLUCOSIDE NUCLEUS OF CHAETIACANDIN [J].

FRIESEN, RW ;

DALJEET, AK .

TETRAHEDRON LETTERS, 1990, 31 (43) :6133-6136

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