1567688-00-9

Basic information

• Product Name: (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate
• Synonyms: (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate
• CAS NO: 1567688-00-9
• Molecular Weight: 543.703
• Mol File: 1567688-00-9.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate(1567688-00-9)
• EPA Substance Registry System: (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate(1567688-00-9)

Safety Data

• Hazardous Substances Data: 1567688-00-9(Hazardous Substances Data)

Upstream product

• 1105054-59-8 (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 537030-19-6 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 

Downstream Products

• 1567685-33-9 2-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-(3-phenylpropyl)pyrrolidin-2-yl)-N-methylacetamide 
• 1567688-03-2 (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate 
• 1567688-04-3 (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1567687-33-5 2-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid 
• 1567688-08-7 (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-(methylamino)-2-oxoethyl)pyrrolidine-1-carboxylate 
• 1567688-10-1 2-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-yl)-N-methylacetamide 
• 1394841-33-8 2-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-(3-phenylpropyl)pyrrolidin-2-yl)-N-methylacetamide 
• 1620081-28-8 (1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-(methylsulfonyloxy)hexahydro-1H-pyrrolizine 

Relevant articles and documents

UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies

A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.

Synthesis and inhibition study of bicyclic iminosugar-based alkaloids, scaffolds, and libraries towards glucosidase

A small library of bicyclic iminosugar-based alkaloids and scaffolds possessing a polyhydroxylated pyrrolidine and a varied ring skeleton have been synthesized. Through rapid diversification of the scaffold via an amide coupling with random carboxylic acids, structurally diverse bicyclic iminosugar-based libraries were prepared with substituent diversity, core diversity, and configurational diversity. This discovery process allowed us to efficiently sieve out potent and specific glycosidase inhibitors, and a bicyclic, conformationally restricted iminosugar was demonstrated to be more potent than the monocyclic ones in this study. The most potent and selective inhibitor discovered was found to have a Ki value of 71 nM against α-glucosidase.

Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules

A straightforward synthesis of novel, 2-heterocyclyl polyhydroxylated pyrrolidines is described. Stereocontrolled additions of nucleophiles to cyclic nitrones generated the corresponding 2,3-trans adducts, allowing the synthesis of the corresponding pyrrolidines via key intermediates bearing an alkyne and a nitrile oxide. Three hybrid systems, including a pyrrolidine with two isoxazoles and one triazole, are efficiently prepared via 1,3-dipolar cycloaddition. Biological testing of the product alkaloids showed that subtle structural variations have drastic effects on their inhibitory activities against glucosidases. This journal is

GLYCOSIDASE INHIBITORS AND USES THEREOF

The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.