Generation and cycloaddition reactions of pyranose-1-carbonitrile oxides

被引：29

作者：

Baker, KWJ ^{[1
]}

Gibb, A ^{[1
]}

March, AR ^{[1
]}

Paton, RM ^{[1
]}

机构：

[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

cycloadditions; C-glycosides; nitrile oxides; isoxazoles; isoxazolines;

D O I：

10.1016/S0040-4039(01)00631-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stannate(II) reduction of the beta -D-glucopyranosylnitromethane derivative 4 affords aldoxime 5, which provides access to the nitrile oxide 7, either on treatment with aq. hypochlorite, or via conversion to the hydroximoyl chloride 11 followed by base-mediated dehydrohalogenation. D-Galactose-, D-mannose- and D-xylose-derived nitrile oxides are generated similarly. The nitrile oxides either dimerise to 3,4-dipyranosyl-1,2,5-oxadiazole N-oxides or are trapped as cycloadducts in the presence of dipolarophiles. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4065 / 4068

页数：4

共 22 条

[1] A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].

BARTRA, M ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON, 1990, 46 (02) :587-594

[2]

Caramella P., 1984, 1 3 DIPOLAR CYCLOADD

[3]

CHAPLEUR Y, 1998, CARBONYDRATE MIMICS

[4]

CURRAN DP, 1988, ADV CYCLOADDITION, V1, P129

[5] SYNTHESIS OF C-DISACCHARIDES USING NITRILE OXIDE CYCLO-ADDITION CHEMISTRY [J].

DAWSON, IM ;

JOHNSON, T ;

PATON, RM ;

RENNIE, RAC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) :1339-1340

[6] Thiazolylketoses: a new class of versatile intermediates for glycoside synthesis [J].

Dondoni, A ;

Marra, A .

CHEMICAL COMMUNICATIONS, 1999, (21) :2133-2145

[7] STEREOCHEMISTRY AND PREPARATION OF 2,6-ANHYDRO-1-DEOXY-1-NITROALDITOLS [J].

FORTSCH, A ;

KOGELBERG, H ;

KOLL, P .

CARBOHYDRATE RESEARCH, 1987, 164 :391-402

[8]

Grunanger P, 1991, ISOXAZOLES CHEM HE 1, V49

[9]

JAGER V, 1994, B SOC CHIM BELG, V103, P491

[10] RECENT ADVANCES IN SYNTHETIC APPLICATIONS OF NITRILE OXIDE CYCLOADDITION (1981-1989) [J].

KANEMASA, S ;

TSUGE, O .

HETEROCYCLES, 1990, 30 (01) :719-736

← 1 2 3 →