Synthesis of a branched chain aza-C-disaccharide via the cycloaddition of a chiral nitrone to an alkene, both sugar derivatives

被引：14

作者：

Argyropoulos, NG ^{[1
]}

Sarli, VC ^{[1
]}

机构：

[1] Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 22期

关键词：

D O I：

10.1016/j.tetlet.2004.04.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A multistep synthesis of a protected aza-C-disaccharide derivative with a pyrrolidine ring as the azasugar component is described. The key step is a stereoselective cycloaddition reaction of a chiral nitrone derived from D-ribose and a sugar alkene derived from D-galactose. An intramolecular N-alkylation followed by a reductive cleavage of the isoxazolidine N-O bond, in one pot, gave the final product. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4237 / 4240

页数：4

共 29 条

[1] Aza-C-disaccharides: Synthesis of 6-deoxygalactonojirimycin beta-C(1->3) linked with D-altrofuranosides and D-galactose [J].

Baudat, A ;

Vogel, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6252-6260

[2] Synthesis of beta-D-(1->3)-C-linked 1,5,6-trideoxy-1,5-iminogalactoside of D-altrose derivatives [J].

Baudat, A ;

Vogel, P .

TETRAHEDRON LETTERS, 1996, 37 (04) :483-484

[3]

Breuer E., 1989, NITRONES NITRONATES, P245

[4] Straightforward synthesis of (1→2)-linked pseudo aza-C-disaccharides by the novel cycloaddition of enantiopure cyclic nitrones to glycals [J].

Cardona, F ;

Valenza, S ;

Picasso, S ;

Goti, A ;

Brandi, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7311-7318

[5] Synthesis of aza-C-galacto disaccharides from C1-substituted galactals [J].

Cheng, XH ;

Kumaran, G ;

Mootoo, DR .

CHEMICAL COMMUNICATIONS, 2001, (09) :811-812

[6]

Chrétien F, 1998, CARBOHYDRATE MIMICS, P143

[7]

CONFALONE PN, 1988, 3 2 NITRONE OLEFIN C, V36

[8] Convergent synthesis of pyrrolidine-based (1→6)- and (1→5)-aza-C-disaccharides [J].

Dondoni, A ;

Giovannini, PP ;

Marra, A .

TETRAHEDRON LETTERS, 2000, 41 (32) :6195-6199

[9] Synthesis of aza-C-disaccharides using cycloaddition reactions of a functionalized cyclic nitrone [J].

Duff, FJ ;

Vivien, V ;

Wightman, RH .

CHEMICAL COMMUNICATIONS, 2000, (21) :2127-2128

[10]

FRENOT E, 1996, TETRAHEDRON LETT, V37, P2023

← 1 2 3 →