A convenient synthesis of iminosugar-C-glycosides via organometallic addition to N-benzyl-N-glycosylhydroxylamines

被引：46

作者：

Dondoni, A ^{[1
]}

Perrone, D ^{[1
]}

机构：

[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 24期

关键词：

nitrones; N-benzyl-N-glycosylhydroxylamines; iminosugars; glycosidase inhibitors; organometallic addition;

D O I：

10.1016/S0040-4020(03)00631-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Benzyl-N-glycosylhydroxylamines were prepared in very good yield via condensation of furanoses and pyranoses with N-benzylhydroxylamine at 110degreesC for 30 min under solvent-free conditions. These anomeric sugar-hydroxylamines exist in equilibrium with the open-chain nitrone form. In fact upon treatment with various organometallic reagents, the corresponding adducts were obtained with good to high diastereoselectivity. These adducts were converted into iminosugar-C-glycosides by reductive dehydroxylation and intramolecular cyclization. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4261 / 4273

页数：13

共 45 条

[31] Glycomimetics: A versatile de novo synthesis of beta-1-C-aryl-deoxymannojirimycin analogues [J].

Johnson, CR ;

Johns, BA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6046-6050

[32] PREPARATION OF 2,3,4,6-TETRA-O-BENZYL-D-MANNOSE [J].

KOTO, S ;

MORISHIMA, N ;

MIYATA, Y ;

ZEN, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (09) :2639-2640

[33]

Legler G, 1998, CARBOHYDRATE MIMICS, P463

[34]

Lombardo M, 2000, SYNTHESIS-STUTTGART, P759

[35] A facile synthesis of glycosyl hydroxylamines [J].

Merino, P ;

Franco, S ;

Merchan, FL ;

Tejero, T .

SYNTHETIC COMMUNICATIONS, 1997, 27 (20) :3529-3537

[36] Synthesis and antimetastatic activity of L-iduronic acid-type 1-N-iminosugars [J].

Nishimura, Y ;

Satoh, T ;

Adachi, H ;

Kondo, S ;

Takeuchi, T ;

Azetaka, M ;

Fukuyasu, H ;

Iizuka, Y .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (16) :2626-2633

[37]

OHRUI H, 1975, J AM CHEM SOC, V97, P4602, DOI 10.1021/ja00849a023

[38]

Sears P, 1999, ANGEW CHEM INT EDIT, V38, P2301

[39] Piperidine analogues of D-galactose as potent inhibitors of α-galactosidase:: Synthesis by stannane-mediated hydroxymethylation of 5-azido-1,4-lactones.: Structural relationships between D-galactosidase and L-rhamnosidase inhibitors [J].

Shilvock, JP ;

Nash, RJ ;

Watson, AA ;

Winters, AL ;

Butters, TD ;

Dwek, RA ;

Winkler, DA ;

Fleet, GWJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (19) :2747-2754

[40] Synthesis of homorhamnojirimycins and related trihydroxypipecolic acid derivatives via divergent bicyclic amino lactone intermediates:: Inhibition of naringinase (L-rhamnosidase) and dTDP-rhamnose biosynthesis [J].

Shilvock, JP ;

Wheatley, JR ;

Nash, RJ ;

Watson, AA ;

Griffiths, RC ;

Butters, TD ;

Müller, M ;

Watkin, DJ ;

Winkler, DA ;

Fleet, GWJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (19) :2735-2745

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