106732-71-2

Basic information

• Product Name: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, [4-(methylthio)phenyl]methyl ester
• CAS NO: 106732-71-2
• Molecular Formula: C25H25NO4S
• Molecular Weight: 435.544
• Mol File: 106732-71-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, [4-(methylthio)phenyl]methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, [4-(methylthio)phenyl]methyl ester(106732-71-2)
• EPA Substance Registry System: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, [4-(methylthio)phenyl]methyl ester(106732-71-2)

Safety Data

• Hazardous Substances Data: 106732-71-2(Hazardous Substances Data)

Upstream product

• 3446-90-0 4-(methylthio)benzyl alcohol 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 106732-72-3 Z-Phe-OMsib 

Relevant articles and documents

The p-(Methylsulfinyl)benzyl Group: A TFA-Stable Carboxyl-Protecting Group Readily Convertible to a TFA-Labile Group

The p-(methylsulfinyl)benzyl or Msib ester is recommended as a selectively cleavable carboxyl-protecting group for peptide synthesis.Peptide oramino acid esters of p-(methylsulfinyl)benzyl alcohol, HO-Msib (2), or p-(methylthio)benzyl alcohol, HO-Mtb (1), are readily prepared from the corresponding alcohols or alkyl halides.Msib esters may also be obtained from Mtb esters by oxidation with m-chloroperbenzoic acid.Msib esters are readily deoxygenated by excess Me3SiCl/Ph3P, Me3SiCl/Me2S, or anhydrous hydrogen chloride.Msib esters are exceedingly stable to TFA while Mtb esters solvolyze rapidly.A sample peptide synthesis demonstrates the protection of the C-terminal carboxyl group during synthesis as the Msib ester followed by Msib group removal on completion of synthesis by deoxygenation and TFA solvolysis.The stability of Mtb and Msib esters to typical acid conditions of peptide synthesis is described.The stability of Msib esters to various peptide synthesis conditions suggests that the Msib group should be quite useful as a carboxyl-protecting group in peptide synthesis.