Synthesis of iminopolyols via Henry reaction:: a short route to the α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues

被引：50

作者：

Kiess, FM

Poggendorf, P

Picasso, S

Jäger, V

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[2] Univ Lausanne, Inst Organ Chem, CH-1015 Lausanne, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 01期

关键词：

D O I：

10.1039/a706915d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alpha-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol (DIM) as well as amino analogues of DIM and of deoxy-manno-nojirimycin, respectively, have been prepared using a diastereoselective nitroaldol addition as the key step.

引用

页码：119 / 120

页数：2

共 41 条

[1] DESOXYNITRO SUGARS .3. SYNTHESIS OF KETOSES BY CHAIN ELONGATION OF 1-DEOXY-1-NITROALDOSES - NUCLEOPHILIC ADDITIONS AND SOLVOLYSIS OF NITRO ETHERS
AEBISCHER, B
BIERI, JH
PREWO, R
VASELLA, A
[J]. HELVETICA CHIMICA ACTA, 1982, 65 (07) : 2251 - 2272
[2] NEW AZIRIDINE SYNTHESIS
APPEL, R
KLEINSTU.R
[J]. CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (01): : 5 - 12
[3] GENERATION AND CYCLOADDITIONS OF 4,5-DIHYDROOXAZOLE-4-CARBONITRILE AND OXAZOLIDINE-4-CARBONITRILE N-OXIDES
BLAKE, AJ
BOYD, EC
GOULD, RO
PATON, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19): : 2841 - 2847
[4] SYNTHESE DE LA L-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHANYL-GLYCYL-EPSILON-CBO-L-LYSYL-L-PROLYL-L-VALYLAMIDE
BOISSONNAS, RA
GUTTMANN, S
HUGUENIN, RL
JAQUENOUD, PA
SANDRIN, E
[J]. HELVETICA CHIMICA ACTA, 1958, 41 (06) : 1867 - 1882
[5] 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
[6] POTENTIAL GLYCOSIDASE INHIBITORS - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO DERIVATIVES OF D-GLUCITOL, D-XYLITOL AND L-XYLITOL, D-ALLITOL AND L-ALLITOL, D-TALITOL AND L-TALITOL, AND D-GULITOL
BUCHANAN, JG
LUMBARD, KW
STURGEON, RJ
THOMPSON, DK
WIGHTMAN, RH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03): : 699 - 706
[7] STEREOSELECTIVE APPROACHES TO BIOACTIVE CARBOHYDRATES AND ALKALOIDS - WITH A FOCUS ON RECENT SYNTHESES DRAWING FROM THE CHIRAL POOL
CASIRAGHI, G
ZANARDI, F
RASSU, G
SPANU, P
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1677 - 1716
[8] CHEN YW, 1992, TETRAHEDRON LETT, V33, P4917
[9] AN IMPROVED, SIMPLIFIED SYNTHESIS OF 1,2-5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL
CHITTENDEN, GJF
[J]. CARBOHYDRATE RESEARCH, 1980, 84 (02) : 350 - 352
[10] PEROXYTRIFLUOROACETIC ACID .6. THE OXIDATION OF OXIMES TO NITROPARAFFINS
EMMONS, WD
PAGANO, AS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (17) : 4557 - 4559

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