General approach to glycosidase inhibitors. Enanti...[J Org Chem. 2005]

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1: J Org Chem. 2005 Mar 18;70(6):2325-8. Links

General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine.

Martín R, Murruzzu C, Pericàs MA, Riera A.

Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Parc Científic de Barcelona, and Departament de Química Orgànica, Universitat de Barcelona, c/Josep Samitier, 1-5, 08028-Barcelona, Spain.

[reaction: see text] Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

PMID: 15760222 [PubMed - indexed for MEDLINE]

A concise enantioselective entry to the synthesis of deoxy-azasugars.
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Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors.
Carbohydr Res. 2007 Sep 3; 342(12-13):1805-12. Epub 2007 Apr 29.

[Carbohydr Res. 2007]
Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose.
Org Lett. 2001 Oct 18; 3(21):3353-6.

[Org Lett. 2001]
ReviewTherapeutic applications of sugar-mimicking glycosidase inhibitors.
Mini Rev Med Chem. 2001 Jul; 1(2):145-54.

[Mini Rev Med Chem. 2001]
ReviewPlagiarizing plants: amino sugars as a class of glycosidase inhibitors.
Ciba Found Symp. 1990; 154:112-22; discussion 122-5.

[Ciba Found Symp. 1990]
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Cited by 2 PubMed Central articles

De Novo Asymmetric Syntheses of d-, l- and 8-epi-Swainsonine.
Guo H, O'Doherty GA. Tetrahedron. 2008 Jan 7; 64(2):304-313.

[Tetrahedron. 2008]
De novo asymmetric synthesis of D- and L-swainsonine.
Guo H, O'Doherty GA. Org Lett. 2006 Apr 13; 8(8):1609-12.

[Org Lett. 2006]

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