787554-04-5

Basic information

• Product Name: NALPHA-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-O-(TERT-BUTYLDIPHENYLSILYL)-PROS-METHYL-L-HISTIDINOL
• Synonyms: NALPHA-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-O-(TERT-BUTYLDIPHENYLSILYL)-PROS-METHYL-L-HISTIDINOL;Nα-(2,4,6-Triisopropylbenzenesulfonyl)-O-(tert-butyldiphenylsilyl)-pros-methyl-L-histidinol;α-(2,4,6-Triisopropylbenzenesulfonyl)-o-(tert-butyldiphenylsilyl)-pros-Methyl-L-histidinol;Nα-(2,4,6-Triisopropylbenzenesulfonyl)-O-(tert-butyldiphenylsilyl)-π-Methyl-L-histidinol;N-[(1S)-2-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-[(1-methyl-1H-imidazol-5-yl)methyl]ethyl]-2,4,6-tris(1-methylethyl)benzenesulfonamide;Benzenesulfonamide,N-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-[(1-methyl-1H-imidazol-5-yl)methyl]ethyl]-2,4,6-tris(1-methylethyl)-
• CAS NO: 787554-04-5
• Molecular Formula: C38H53N3O3SSi
• Molecular Weight: 660
• Product Categories: Asymmetric Synthesis;for Resolution of Alcohols & Thiols;Monoalkoxysilanes;Optical Resolution;Si (Classes of Silicon Compounds);Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 787554-04-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 177 °C
• Boiling Point: 719.2oC at 760 mmHg
• Flash Point: 388.8oC
• Appearance: /
• Density: 1.07g/cm3
• Vapor Pressure: 1.55E-20mmHg at 25°C
• Refractive Index: 5 ° (C=1, CHCl3)
• PKA: 10.52±0.50(Predicted)
• CAS DataBase Reference: NALPHA-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-O-(TERT-BUTYLDIPHENYLSILYL)-PROS-METHYL-L-HISTIDINOL(CAS DataBase Reference)
• NIST Chemistry Reference: NALPHA-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-O-(TERT-BUTYLDIPHENYLSILYL)-PROS-METHYL-L-HISTIDINOL(787554-04-5)
• EPA Substance Registry System: NALPHA-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-O-(TERT-BUTYLDIPHENYLSILYL)-PROS-METHYL-L-HISTIDINOL(787554-04-5)

Safety Data

• Hazardous Substances Data: 787554-04-5(Hazardous Substances Data)

Usage

Uses

N-alpha-(2,4,6-Triisopropylbenzenesulfonyl)-O-(tert-butyldiphenylsilyl)-pros-methyl-L-histidinol (CAS# 787554-04-5) is a histidine-derived compound used as a catalyst in enantioselective esterification.

InChI:InChI=1/C38H53N3O3SSi/c1-27(2)30-21-35(28(3)4)37(36(22-30)29(5)6)45(42,43)40-31(23-32-24-39-26-41(32)10)25-44-46(38(7,8)9,33-17-13-11-14-18-33)34-19-15-12-16-20-34/h11-22,24,26-29,31,40H,23,25H2,1-10H3/t31-/m0/s1

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 787554-00-1 (+)-N(?)-methyl-N(α)-(2,4,6-triisopropylbenzenesulfonyl)-L-histidinol 

Relevant articles and documents

Kinetic resolution of racemic alcohols catalyzed by minimal artificial acylases derived from l-histidine

The artificial acylases, tert-butyldiphenylsilyl ether and tris(trimethylsilyl)silyl ether of N(π)-methyl-N(α)-(2,4,6-triisopropylbenzenesulfonyl)-l-histidinol, are simple and small molecules, which contain only one chiral carbon center that originates from natural l-histidine. Asymmetric acylation of racemic secondary alcohols with isobutyric anhydride induced by these artificial acylases gave optically active isobutyrates and optically active alcohols with an S(kfast-reacting enantiomer/kslow-reacting enantiomer) value of up to 132. One hydrogen bonding interaction between a sulfonamidyl group of the catalysts and a substrate should be essential for inducing the high level of kinetic resolution through catalytic asymmetric acylation. Furthermore, a reusable polystyrene-bound artificial acylase was developed to examine its practicality.