Organotransition metal modified sugars 4. Carbene complex functionalized acyclic carbohydrates

被引：9

作者：

Dotz, KH

Ehlenz, R

Straub, W

Weber, JC

Airola, K

Nieger, M

机构：

[1] Univ Bonn, Inst Organ Chem & Biochem, D-53121 Bonn, Germany

[2] Univ Bonn, Inst Anorgan Chem, D-53121 Bonn, Germany

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1997年 / 548卷 / 01期

关键词：

optically active carbene complexes; carbohydrates; glycosyl carbene complexes; conformation of carbohydrates;

D O I：

10.1016/S0022-328X(97)00335-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A synthetic strategy based on a combination of sugar electrophiles and transition metal nucleophiles allows the metal carbene functionalization of acyclic carbohydrates. Following this methodology the per-O-acetylated methoxycarbene complexes 8-14 are prepared in moderate to good yields. Upon reaction with ammonia they undergo aminolysis to give the aminocarbene complexes 16-18. H-1-NMR studies indicate that in solution the D-galacto and L-arabino complexes adopt extended planar zigzag conformations. A similar conformational preference is observed for the solid state as established by X-ray studies on the D-galacto derivatives 8 and 15. (C) 1997 Elsevier Science S.A.

引用

收藏

页码：91 / 98

页数：8

相关论文

共 41 条

[1] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .70. -[2-(GALACTOPYRANOSYLAMINO)ETHENYL]CARBENE AND 3-(GALACTOPYRANOSYLAMINO)-1,2-PROPADIENYLIDENE COMPLEXES ON 3-ADDITION OF 2,3,4,6-TETRA-O-PIVALOYL-BETA-D-GALACTOPYRANOSYLAMINE TO ALKYNYLCARBENE COMPLEXES (M=CR, W) - ATROPISOMERIC GALACTOPYRANOSYL PYRROLES BY REACTION OF [2-(GALACTOPYRANOSYL-AMINO)ETHENYL]CARBENE COMPLEXES WITH ISOCYANIDES [J].

AUMANN, R .

CHEMISCHE BERICHTE, 1994, 127 (04) :725-729

[2] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .62. 1ST CARBENE COMPLEXES (M = CR, W) WITH CARBOHYDRATE SUBSTITUENTS [J].

AUMANN, R .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2773-2778

[3] CHAIN ELONGATION BY USE OF AN IRON CARBONYL REAGENT - A FACILE SYNTHESIS OF 6-DEOXYHEPTOSIDURONIC ACIDS [J].

BAER, HH ;

HANNA, HR .

CARBOHYDRATE RESEARCH, 1982, 102 (APR) :169-183

[4] EFFICIENT SYNTHESIS OF SOME DICHLOROALDITOLS - DIRECT REGIOSELECTIVE CHLORINATION OF SOME UNPROTECTED ALDITOLS BY 1-CHLOROCARBONYL-1-METHYLETHYL ACETATE [J].

BENAZZA, M ;

MASSOUI, M ;

UZAN, R ;

DEMAILLY, G .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (07) :967-979

[5] CONFORMATION OF ACYCLIC DERIVATIVES OF SUGARS .12. CONFORMATIONAL INSTABILITY OF POLYSUBSTITUTED CARBON CHAINS - TEMPERATURE-DEPENDENCE OF CONFORMATION OF TETRA-O-ACETYL-D-RIBOSE DIISOBUTYL DITHIOACETAL [J].

BLANCMUESSER, M ;

DEFAYE, J ;

HORTON, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :3053-3055

[6] CONFORMATION OF ACYCLIC DERIVATIVES OF SUGARS .15. CONFORMATIONS IN SOLUTION OF THE STEREOISOMERIC, PERACETYLATED ALDOHEXOSE DIMETHYL ACETALS AND DIETHYL DITHIOACETALS [J].

BLANCMUESSER, M ;

DEFAYE, J ;

HORTON, D .

CARBOHYDRATE RESEARCH, 1980, 87 (01) :71-86

[7] C-GLYCOSIDES FROM PALLADIUM-MEDIATED REACTIONS OF PYRANOID GLYCALS - STEREOCHEMISTRY OF FORMATION OF INTERMEDIATE ORGANOPALLADIUM ADDUCTS AND FACTORS AFFECTING THEIR STABILITY AND DECOMPOSITION [J].

CHENG, JCY ;

DAVES, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3083-3090

[8] CONFORMATION OF SOME BENZOYLATED ALDONONITRILES AND 5-(POLYBENZOYLOXYALKYL)TETRAZOLES AS DETERMINED BY THEIR H-1-NMR SPECTRA [J].

DACCORSO, NB ;

THIEL, IME .

CARBOHYDRATE RESEARCH, 1987, 167 :301-304

[9] 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

[10] STEREOSELECTIVITY IN THE FORMATION OF PENTACARBONYL GLYCOSYLMANGANESE COMPLEXES [J].

DESHONG, P ;

SLOUGH, GA ;

ELANGO, V .

CARBOHYDRATE RESEARCH, 1987, 171 :342-345

← 1 2 3 4 5 →