275827-13-9

Basic information

• Product Name: N-(tert-Butyloxycarbonyl)-D-phenylalanin-(2-phenyl-2-trimethylsilyl)ethylester
• Synonyms: N-(tert-Butyloxycarbonyl)-D-phenylalanin-(2-phenyl-2-trimethylsilyl)ethylester
• CAS NO: 275827-13-9
• Molecular Weight: 441.643
• Mol File: 275827-13-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(tert-Butyloxycarbonyl)-D-phenylalanin-(2-phenyl-2-trimethylsilyl)ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butyloxycarbonyl)-D-phenylalanin-(2-phenyl-2-trimethylsilyl)ethylester(275827-13-9)
• EPA Substance Registry System: N-(tert-Butyloxycarbonyl)-D-phenylalanin-(2-phenyl-2-trimethylsilyl)ethylester(275827-13-9)

Safety Data

• Hazardous Substances Data: 275827-13-9(Hazardous Substances Data)

Upstream product

• 591-51-5 phenyllithium 
• 16722-09-1 trimethylsilyloxirane 
• 18942-49-9 Boc-D-Phe-OH 
• 122760-31-0 2-phenyl-2-(trimethylsilyl)ethanol 
• 754-05-2 ethenyltrimethylsilane 

Downstream Products

• 18942-49-9 Boc-D-Phe-OH 

Relevant articles and documents

The (2-phenyl-2-trimethylsiylyl)ethyl (PTMSE) ester - A carboxy protecting group cleavable under neutral conditions

(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters of aminoacids and peptides are stable under the conditions of hydrogenolytic cleavage of benzoxycarbonyl(Z) and benzyl ester groups, base-induced removal of Fmoc groups, palladium(0)-catalyzed removal of allyloxycarbonyl (Aloc) and even acidolytic cleavage of Boc groups. PTMSE esters are also stable under the conditions of peptide condensation reactions. The PTMSE ester is selectively cleaved by treatment with tetrabutylammonium fluoride (TBAF) trihydrate in dichloromethane, i.e. under almost neutral conditions, within a few minutes and, therefore, considered a valuable novel carboxy protecting group.