221375-48-0

Basic information

• Product Name: (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide
• Synonyms: (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide
• CAS NO: 221375-48-0
• Molecular Weight: 223.339
• Mol File: 221375-48-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide(221375-48-0)
• EPA Substance Registry System: (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide(221375-48-0)

Safety Data

• Hazardous Substances Data: 221375-48-0(Hazardous Substances Data)

Upstream product

• 122-78-1 phenylacetaldehyde 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 

Downstream Products

• 87923-45-3 R-(-)-1-phenyl-2-aminobutane hydrochloride 
• 87923-46-4 S-(+)-1-phenyl-2-aminobutane hydrochloride 
• 68839-08-7 (S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester 

Relevant articles and documents

Synthesis of a Chloroalkene Dipeptide Isostere-Containing Peptidomimetic and Its Biological Application

The first rapid and efficient chemical synthesis of a cyclic Arg-Gly-Asp (RGD) peptide containing a chloroalkene dipeptide isostere (CADI) is reported. By a developed synthetic method, an N-tert-butylsulfonyl protected CADI was obtained utilizing diastereoselective allylic alkylation as a key reaction. This CADI was also transformed into an N-Fmoc protected CADI in a few steps. The CADI was used in Fmoc-based solid-phase peptide synthesis. The first synthesis of a CADI-containing cyclic RGD peptide was successful, and the synthesized CADI-containing peptidomimetic was found to be a more potent inhibitor against integrin-mediated cell attachment than the parent cyclic peptide.

Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics

Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.

Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

Nucleophilic addition reactions of 2-lithiated N-phenylsulfonylindoles with (R)-N-tert-butanesulfinyl aldimines provided chiral (2-indolyl) methanamine derivatives in moderate to good yields (up to 100%) with excellent diastereoselectivities (>99:1), in which no additional Lewis acids were required.