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CAS RN: 1883396-49-3 | Product Number: P2380

(S)-[4-(Pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine-2,6-diyl]bis[bis[4-(tert-butyl)phenyl]methanol]


Purity: >85.0%(HPLC)
Synonyms:
Product Documents:
50MG
¥54,800
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Product Number P2380
Purity / Analysis Method >85.0%(HPLC)
Molecular Formula / Molecular Weight C__6__9H__7__2N__2O__2 = 961.35 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN 1883396-49-3
PubChem Substance ID 354333549
Specifications
Appearance Light orange to Yellow to Green powder to crystal
Purity(HPLC) min. 85.0 area%
Elemental analysis(Nitrogen) 2.50 to 3.30 %
Specific rotation [a]20/D -270 to -310 deg(C=0.2, CHCl3)
NMR confirm to structure
Properties (reference)
Specific Rotation -290° (C=0.2,CHCl3)
GHS
Related Laws:
Transport Information:
Application
A Highly Active 4-Dimethylaminopyridine (DMAP) Derivative Chiral Nucleophilic Catalyst

These asymmetric organocatalysts [P2380] and [P2617] are novel chiral DMAP derivatives, developed by Mandai and Suga et al.1) They show extremely high catalytic activity (0.1-0.5 mol % catalyst) and enantioselectivity in chiral acylating reactions, such as Steglich rearrangements1), the kinetic resolution of secondary carbinols2) and D,L-1,2-diols3), and the desymmetrization of meso-1,2-diols.4)

References


Application
Enantioselective Steglich Rearrangement with a Highly Active Chiral Nucleophilic Catalyst

P2380

Typical Procedure(Steglich rearrangement,1) R=CH3):
To a solution of phenyl 2-((phenoxycarbonyl)oxy)-3-methyl-1H-indole-1-carboxylate (37.4 mg, 0.1 mmol) in THF (0.25 mL) is added a solution of the DMAP chiral analog [P2380] (0.48 mg, 0.5 µmol) in THF at -20 °C. The reaction mixture was stirred for 5 h at -20 °C and then 1 M aqueous HCl is added. The resulting mixture is extracted with EtOAc, dried over MgSO4 and concentrated in vacuo. The purification of the crude product by flash column chromatography on a short pad of silica gel (eluent: hexane/Et2O = 1/1) gives (S)-diphenyl 3-methyl-2-oxoindoline-1,3-dicarboxylate (36.9 mg, 99% yield).

References


PubMed Literature


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