New access to aza-C-disaccharides by cycloadditions of pyrroline N-oxides to glycals

被引：25

作者：

Cardona, F ^{[1
]}

Valenza, S ^{[1
]}

Goti, A ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN UGO SCHIFF,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(97)10118-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, highly stereoselective intermolecular cycloaddition reaction of simple and enantiopure cyclic nitrones to glucose and galactose-derived 1,2-glycals offers a direct access to a new class of pseudoaza-C-disaccharides with isoxazolidine structure, potential glycosidase inhibitors. The synthesis of new (1-->2)-linked aza-disaccharides is accomplished by simple reductive ring-opening of the isoxazolidine. (C) 1997 Elsevier Science Ltd.

引用

页码：8097 / 8100

页数：4

共 22 条

[1] Synthesis of beta-D-(1->3)-C-linked 1,5,6-trideoxy-1,5-iminogalactoside of D-altrose derivatives
Baudat, A
Vogel, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (04) : 483 - 484
[2] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF NATURAL LENTIGINOSINE BY SYNTHESIS AND ENZYMATIC ASSAYS OF OPTICALLY PURE (+)-ENANTIOMERS AND (-)-ENANTIOMERS
BRANDI, A
CICCHI, S
CORDERO, FM
FRIGNOLI, R
GOTI, A
PICASSO, S
VOGEL, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6806 - 6812
[3] Capozzi G, 1996, ANGEW CHEM INT EDIT, V35, P777
[4] THE SYNTHESIS OF OPTICALLY PURE BETA-LACTAMS DERIVED FROM SUGARS - HIGH-PRESSURE [2+2] CYCLOADDITION OF TOLUENE-4-SULFONYL ISOCYANATE TO GLYCALS
CHMIELEWSKI, M
KALUZA, Z
BELZECKI, C
SALANSKI, P
JURCZAK, J
[J]. TETRAHEDRON LETTERS, 1984, 25 (42) : 4797 - 4800
[5] NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID
CICCHI, S
HOLD, I
BRANDI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) : 5274 - 5275
[6] A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE
CICCHI, S
GOTI, A
BRANDI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4743 - 4748
[7] Total asymmetric synthesis of long-chain, branched carbohydrates and of an aza-C-disaccharide
Frerot, E
Marquis, C
Vogel, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (12) : 2023 - 2026
[8] Goti A, 1996, SYNLETT, P761
[9] THE TOTAL SYNTHESIS OF (-)-CRYPTOSPORIN
GUPTA, RB
FRANCK, RW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) : 7668 - 7670
[10] ENANTIOSPECIFIC SYNTHESIS OF HETEROCYCLIC-COMPOUNDS - AN APPROACH TO FUNCTIONALIZED TETRAHYDROFURANS FROM INTRAMOLECULAR DIPOLAR CYCLOADDITIONS
HEWSON, AT
JEFFERY, J
SZCZUR, N
[J]. TETRAHEDRON LETTERS, 1995, 36 (42) : 7731 - 7734

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