1101869-66-2

Basic information

• Product Name: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
• Synonyms: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
• CAS NO: 1101869-66-2
• Molecular Weight: 283.324
• Mol File: 1101869-66-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol(1101869-66-2)
• EPA Substance Registry System: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol(1101869-66-2)

Safety Data

• Hazardous Substances Data: 1101869-66-2(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 1101869-65-1 (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol 
• 1214915-03-3 (2R,3R,4R,5R)-2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-1-methylpyrrolidine-3,4-diol 

Relevant articles and documents

DDQ-Promoted Benzylic/Allylic sp3 C-H Activation for the Stereoselective Intramolecular C-N Bond Formation: Applications to the Total Synthesis of (-)-Codonopsinine, (+)-5-epi-Codonopsinine, (+)-Radicamine B, and (-)-Codonopsinol

This is the first report on an intramolecular C-N bond formation of an amide-tethered benzylic/allylic system using DDQ under neutral conditions which has been successfully applied to the total synthesis of naturally occurring pyrolidine alkaloids. The key steps for the synthesis of corresponding precursors involve Julia-Kociensky olefination/cross-metathesis and dihydroxylation reactions, and this methodology is also extended to the ω-unsaturated N-sulfanilamide to furnish piperidines.

Total synthesis of (-)-codonopsinol and (+)-2-epi codonopsinol via acid catalyzed amido cyclisation

A short and stereoselective synthesis of (-)-codonopsinol 5 and its C-2 epimer 6 were accomplished from commercially available starting material d-1,5-gluconolactone, using acid mediated amido cyclisation as the key step. The inhibitory activitiy of these

Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A (20) and B (18) against α-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 μM, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases.