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(S)-3-[1-(4-Methoxybenzenesulfonyl)-(4S,5S)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]-1,1'-binaphthalene-2,2'-diyl Hydrogen Phosphate
(CAS RN:1621994-95-3 Product Number:M2765)

Structure

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(S)-3-[1-(4-Methoxybenzenesulfonyl)-(4S,5S)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]-1,1'-binaphthalene-2,2'-diyl Hydrogen Phosphate

General Information

Product Number M2765

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Purity/Analysis Method >96.0%(HPLC)
Storage Temperature <0°C
M.F. / M.W. C42H31N2O7PS=738.75
CAS RN 1621994-95-3
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MDL Number
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Specification

Appearance White to Yellow to Green powder to crystal
Purity(HPLC) min. 96.0 area%
Elemental analysis(Nitrogen) 3.50 to 4.00 %
Specific rotation [a]20/D +275 to +295 deg(C=0.5, CHCl3)

References

Reaxys-RN 27615196
PubChem SID 354333322

Transport Information

HS Number 2935909099

Application

A Chiral Imidazoline-phosphoric Acid Catalyst Usable for the Desymmetrizating Reaction of meso-Aziridine Derivatives

M2765

Experimental procedure: The mixture of 1 (3.1 mg, 0.0042 mmol) and Ca(OMe)2 (0.4 mg, 0.0042 mmol) in methanol (0.08 mL) is stirred for 1 h. After removal of the solvent under reduced pressure, N-(2-pyridinesulfonyl)cyclohexaneaziridine (20.0 mg, 0.084 mmol) in toluene (1.68 mL) and molecular sieves 4Å (8.4 mg) are successively added, and the whole mixture is stirred at -20 °C. Then, trimethylsilylisothiocyanate (14.2 µL, 0.101 mmol) is added. After the disappearance of aziridine in the reaction mixture monitored by TLC, the water (3.0 mL) is added. The aqueous layer is extracted with CH2Cl2, the combined organic layer is dried over Na2SO4. Removal of solvent under reduced pressure gives the crude product, which is purified by flash chromatography on silica gel (hexane : ethyl acetate = 50 : 50) to afford the corresponding product as a white solid (24.8 mg, 88% ee) in 99% yield.

References

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