Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors.

doi:10.1039/b711994a

Paper

Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors.

Published Oct 17, 2007 · K. Curtis, E. Evinson, S. Handa

Organic & biomolecular chemistry

Q2 SJR score

15

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Three diastereoisomers of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidine have been synthesised by a divergent route starting from trans-4-hydroxy-L-proline. Regio- and stereoselective introduction of the 3-amino and 4-hydroxyl functional groups was achieved using either a tethered aminohydroxylation reaction or by employing intra- and intermolecular epoxide-opening strategies. Preliminary biological data indicate that two of these novel amino pyrrolidines are moderate inhibitors of beta-galactosidase.

Study Snapshot

Two novel amino pyrrolidines show moderate inhibitory effects on beta-galactosidase, offering potential as glycosidase inhibitors.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors.

Sign up to use Study Snapshot

References

Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction.

The Donohoe tethered aminohydroxylation reaction enables a stereocontrolled and scalable synthesis of the dysiherbaine tetrahydropyran core in 11 steps with 27% overall yield.

Tethered aminohydroxylation: dramatic improvements to the process.

Using OCOC6F5 as a leaving group in a hydroxylamine-based reoxidant significantly improves the tethered aminohydroxylation reaction, resulting in higher yields and making acyclic homoallylic alcohols viable substrates for oxidation.

Synthesis of New Pyrrolidine Derivatives as Inhibitors of a-Mannosidase and of the Growth of Human Glioblastoma Cells

The most potent and selective alpha-mannosidase inhibitor (6d) also inhibits human glioblastoma cell growth, making it a potential cancer drug.

α- and β-Glucosidase inhibitors: chemical structure and biological activity

Glucosidase inhibitors show promising therapeutic potential in treating disorders like diabetes, HIV, metastatic cancer, and lysosomal storage diseases.

Glycosylation pathways as drug targets for cancer: glycosidase inhibitors.

Glycosylation pathways and their inhibitors offer potential new targets for cancer therapy, as altered glycosylation patterns contribute to cancer cell growth and aggressive behavior.

Citations

Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides.

Pendant sulfamates and sulfamides enable precise ring opening of epoxides, yielding oxathiazinanes and cyclic sulfamides with excellent diastereoselectivity and regiocontrol under mild conditions.

Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

This study developed a two-step method for preparing 3,4-epoxypyrroline derivatives from 2-halo-2H-azirine-2-carboxylates, diazo keto esters, and amines, resulting in highly functionalized rac-(1R,4R,5S

Asymmetric Synthesis of 3,4-Disubstituted 2-(Trifluoromethyl)pyrrolidines through Rearrangement of Chiral 2-(2,2,2-Trifluoro-1-hydroxyethyl)azetidines.

This study demonstrates a diastereoselective synthesis of chiral 3,4-disubstituted 2-(trifluoromethyl)pyrrolidines with high diastereoselectivity and potential applications in organic synthesis.

[2 + 1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines

This study demonstrates a controlled process for the synthesis of valuable biologically active molecules using (Z)- and (E)-vinyl epoxypyrrolidines, with complete stereoselectivity on the vinyl substituent depending on the diazo compound used.

Organo‐ and Iron(0) Catalysis for an Enantioselective Michael Addition–Hemiketalization–Fragmentation Sequence to Protected ω‐Hydroxy‐nitroketones

This study demonstrates an efficient, enantioselective method for preparing key enantioenriched ketones with additional nitro and protected alcohol functions using organocatalysis and iron(0) catalysis.