1567688-03-2

Basic information

• Product Name: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate
• Synonyms: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate
• CAS NO: 1567688-03-2
• Molecular Weight: 577.718
• Mol File: 1567688-03-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate(1567688-03-2)
• EPA Substance Registry System: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate(1567688-03-2)

Safety Data

• Hazardous Substances Data: 1567688-03-2(Hazardous Substances Data)

Upstream product

• 1567688-00-9 (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate 
• 1105054-59-8 (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol 
• 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 
• 1567688-04-3 (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

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.

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.