An Expeditious Synthesis of Iminosugars

2010 ◽  
Vol 63 (10) ◽  
pp. 1409 ◽  
Author(s):  
Michael N. Gandy ◽  
Matthew J. Piggott ◽  
Keith A. Stubbs
Keyword(s):  
Glycosidase Inhibitors

A short and expedient synthesis of the potent glycosidase inhibitors, 1-deoxynojirimycin, miglitol, miglustat, 1-deoxymannojirimycin, and 1-deoxygalactonojirimycin is presented.

The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

2002 ◽  
Vol 80 (8) ◽  
pp. 857-865 ◽  
Author(s):  
Wayne M Best ◽  
James M Macdonald ◽  
Brian W Skelton ◽  
Robert V Stick ◽  
D Matthew G Tilbrook ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Glycoside Hydrolases ◽  
Crystalline Solid ◽  
Glycosidase Inhibitors ◽  
Protecting Group ◽  
Mild Acid Hydrolysis ◽  
Catalytic Hydrogenolysis ◽  
Palladium On Carbon ◽  
Mild Acid

The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3- O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that, upon heating in water, gave the dihydrooxazine [(4R,5S,6R)-5,6-dihydro-4,5-dihydroxy-6-hydroxymethyl-4H-1,2-oxazine] as a crystalline solid. A single-crystal structure determination of this solid showed it to exist in the 5H6 conformation. Reduction of the dihydrooxazine gave the tetrahydrooxazine [(4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-1,2-oxazine]. The dihydrooxazine was an effective inhibitor of two β-glucosidases (Ki = 27 and 35 µM). Benzyl 2,3-O-isopropylidene-β-L-xylopyranoside, via the derived imidazylate, was converted into a nitrile that, upon reduction and protecting-group manipulations, gave benzyl 4-C-aminomethyl-4-deoxy-α-D-arabinoside. Treatment of this amine with hydrogen and palladium-on-carbon gave isofagomine.Key words: dihydrooxazine, tetrahydrooxazine, isofagomine, iminosugars, glycosidase inhibitors.

Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors

Tetrahedron ◽  
2003 ◽  
Vol 59 (16) ◽  
pp. 2801-2809 ◽  
Author(s):  
Vı́ctor Ulgar ◽  
Óscar López ◽  
Inés Maya ◽  
José G Fernández-Bolaños ◽  
Mikael Bols
Keyword(s):  
Glycosidase Inhibitors

Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors

2012 ◽  
Vol 356 ◽  
pp. 110-114 ◽  
Author(s):  
Hongqing Li ◽  
Yongmin Zhang ◽  
Sylvain Favre ◽  
Pierre Vogel ◽  
Matthieu Sollogoub ◽  
...  
Keyword(s):  
Glycosidase Inhibitors

ChemInform Abstract: Stereocontrolled Synthesis of Glycosidase Inhibitors (+)-Hyacinthacines A1(I) and A2(II).

ChemInform ◽  
2015 ◽  
Vol 46 (24) ◽  
pp. no-no
Author(s):  
Amael Veyron ◽  
Paidi Venkatram Reddy ◽  
Peter Koos ◽  
Alexandre Bayle ◽  
Andrew E. Greene ◽  
...  
Keyword(s):  
Glycosidase Inhibitors ◽  
Stereocontrolled Synthesis

Iminoheptitols as glycosidase inhibitors: Synthesis of, and mannosidase and fucosidase inhibition by, α—homomannojirimycin and 6-epi-homomannojirimycin

1989 ◽  
Vol 30 (51) ◽  
pp. 7257-7260 ◽  
Author(s):  
Ian Bruce ◽  
George W.J. Fleet ◽  
Isabelle Cenci di Bello ◽  
Bryan Winchester
Keyword(s):  
Glycosidase Inhibitors

Synthesis of Selenium Analogues of the Naturally Occurring Glycosidase Inhibitor Salacinol and Their Evaluation as Glycosidase Inhibitors†

2002 ◽  
Vol 124 (28) ◽  
pp. 8245-8250 ◽  
Author(s):  
Blair D. Johnston ◽  
Ahmad Ghavami ◽  
Morten T. Jensen ◽  
Birte Svensson ◽  
B. Mario Pinto
Keyword(s):  
Glycosidase Inhibitors ◽  
Naturally Occurring ◽  
Glycosidase Inhibitor
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