1105054-59-8

Basic information

• Product Name: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol
• Synonyms: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol
• CAS NO: 1105054-59-8
• Molecular Weight: 459.585
• Mol File: 1105054-59-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol(1105054-59-8)
• EPA Substance Registry System: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol(1105054-59-8)

Safety Data

• Hazardous Substances Data: 1105054-59-8(Hazardous Substances Data)

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 537030-19-6 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 1301611-54-0 (2R,3R,4R)-2-allyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 1301611-56-2 (2R,3R,4R)-5-allyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 1301611-57-3 (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-((E)-prop-1-enyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 1301611-60-8 6,7-bis(benzyloxy)-1-benzyloxymethyl-3,8-epoxy-9-nortropane 
• 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 
• 1567688-00-9 (2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate 

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.

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.

Synthesis of d-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2

Several new polyhydroxylated alkaloids including pyrrolidines with a long side chain and 3-(hydroxymethyl) indolizidines were prepared from a common nitrone easily obtained from d-arabinose. In addition, a total synthesis of hyacinthacine A2 has been achieved in five steps and 67.7% overall yield starting from the same d-arabino-derived nitrone. All synthesized compounds have a common structural feature consisting of a pyrrolidine ring with d-arabino configuration.