Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases-Reference-Cited by-同舟云学术

Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases

Published:2010-03 Issue:3 Volume:21 Page:311-319
ISSN:0957-4166
Container-title:Tetrahedron: Asymmetry
language:en
Short-container-title:Tetrahedron: Asymmetry

Author:

Best Daniel,Wang Chen,Weymouth-Wilson Alexander C.,Clarkson Robert A.,Wilson Francis X.,Nash Robert J.,Miyauchi Saori,Kato Atsushi,Fleet George W.J.

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference91 articles.

1. Synthesis of 2s, 4s, 5s -dihydroxypipecolic acid and bulgecinine [2s,4s,5r-4-hydroxy-5- (hydroxymethyl)proline] from d-glucuronolactone, a strategy for the synthesis of 2s,4s-4-hydroxy-α-amino acids

2. Enantiospecific syntheses of 2S,3R,4R,5S-trihydroxypipecolic acid, 2R,3R,4R,5S-trihydroxypipecolic acid, 2S,4S,5S-dihydroxypipecolic acid, and bulgecinine from D-glucuronolactone

3. The synthesis of polyhydroxylated amino acids from glucuronolactone: enantiospecific syntheses of 2s, 3r, 4r, 5s-trihydroxypipecolic acid, 2r, 3r, 4r, 5s-trihydroxypipecolic acid and 2r, 3r, 4r-dihydroxyproline

4. Large scale synthesis of the acetonides of l-glucuronolactone and of l-glucose: easy access to l-sugar chirons

5. Glycomimetics at the Mirror: Medicinal Chemistry of L-Iminosugars

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