959415-37-3

Basic information

• Product Name: 1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(4-methoxybenzyl)selanyl]butan-2-one
• Synonyms: 1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(4-methoxybenzyl)selanyl]butan-2-one
• CAS NO: 959415-37-3
• Molecular Weight: 534.473
• Mol File: 959415-37-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(4-methoxybenzyl)selanyl]butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(4-methoxybenzyl)selanyl]butan-2-one(959415-37-3)
• EPA Substance Registry System: 1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(4-methoxybenzyl)selanyl]butan-2-one(959415-37-3)

Safety Data

• Hazardous Substances Data: 959415-37-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 150308-80-8 N-(9-fluorenylmethoxycarbonyl)-Se-(p-methoxyphenylmethyl)-L-selenocysteine 
• 146552-76-3 Se-(4-methoxybenzyl)-L-selenocysteine 

Relevant articles and documents

Preparation of the β3-homoselenocysteine derivatives Fmoc-β3hSec(PMB)-OH and Boc-β3hSec(PMB)-OH for solution and solid-phase-peptide synthesis and selenoligation

The title compounds, 4 and 7, have been prepared from the corresponding α-amino acid derivative selenocystine (1) by the following sequence of steps: cleavage of the Se-Se bond with NaBH4, p-methoxybenzyl (PMB) protection of the SeH group, Fmoc or Boc protection at the N-atom and Arndt-Eistert homologation (Schemes 1 and 2). A β3-heptapeptide 8 with an N-terminal β3-hSec(PMB) residue was synthesized on Rink amide AM resin and deprotected ('in air') to give the corresponding diselenide 9, which, in turn, was coupled with a β3-tetrapeptide thiol ester 10 by a seleno-ligation. The product β3- undecapeptide was identified as its diselenide and its mixed selenosulfide with thiophenol (Scheme 3). The differences between α- and β-Sec derivatives are discussed.