65935-47-9

Upstream product

• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 699-12-7 2-(phenylthio)ethanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 676531-63-8 carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-phenylsulfanyl-ethyl ester 
• 676531-71-8 (2S,3S)-3-Methyl-2-(2-phenylsulfanyl-ethoxycarbonylamino)-pentanoic acid 
• 676531-73-0 (S)-2-(2-Phenylsulfanyl-ethoxycarbonylamino)-succinic acid 
• 406954-45-8 (S)-3-Phenyl-2-(2-phenylsulfanyl-ethoxycarbonylamino)-propionic acid 
• 406954-46-9 (2-phenylsulfanyl-ethoxycarbonylamino)-acetic acid 
• 406954-44-7 (S)-3-(4-Hydroxy-phenyl)-2-(2-phenylsulfanyl-ethoxycarbonylamino)-propionic acid 

Relevant academic research and scientific papers

Solid-phase peptide synthesis in water. Part 3: A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water

Chemical synthesis of peptides has been performed in various organic solvents, but the safe disposal of organic solvents is now an important environmental issue. Our aim is to be able to perform solid-phase peptide synthesis in water. For this, we have designed a new water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl (Pms), and have studied its introduction onto amino acids. Pms-amino acids were prepared by treating 2-(phenylthio)ethoxycarbonyl amino acids with methyl iodide in the presence of silver tetrafluoroborate. Because sulfur-containing amino acids, such as Met and Cys, were modified by the reaction, we designed a new reagent, 2-[phenyl(methyl)sulfonio]ethyl-4-nitrophenyl carbonate, to introduce the Pms group on amino acids. This reagent is a stable crystalline material and its introduction onto amino acids (including sulfur-containing amino acids) was successful. The solid-phase synthesis of Leu- and Met-enkephalin amides using Pms-protected amino acids was successfully achieved in water.

Synthesis and biological evaluation of an N10-Psec substituted pyrrolo[2,1-c][1,4]benzodiazepine prodrug

The first example of an N10-protected (e.g., Psec, 15) pyrrolo[2,1-c][1,4]benzodiazepine (PBD) analogue that retains significant cytotoxicity in a number of tumour cell lines is reported. This prototype could lead to a new generation of clinically useful N10-protected PBD prodrugs.

Calicheamicin mimics

Synthetic calicheamicin mimics employ alternative activation triggers and trigger cites and include tithers for conjugation to DNA targeting systems.