1310360-92-9

Basic information

• Product Name: N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucine allyl ester
• Synonyms: N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucine allyl ester
• CAS NO: 1310360-92-9
• Molecular Weight: 501.698
• Mol File: 1310360-92-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucine allyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucine allyl ester(1310360-92-9)
• EPA Substance Registry System: N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucine allyl ester(1310360-92-9)

Safety Data

• Hazardous Substances Data: 1310360-92-9(Hazardous Substances Data)

Upstream product

• 18666-68-7 vinyltriphenylsilane 
• 18666-87-0 1,1,1-triphenyl-1-silapropan-3-ol 
• 1310360-86-1 4-nitrophenyl 2-(triphenylsilyl)ethyl carbonate 
• 88224-03-7 L-leucine allyl ester hydro-p-toluenesulfonate 

Downstream Products

• 1310361-10-4 N-(2-(triphenylsilyl)ethoxy)carbonyl-L-leucyl-L-leucine tert-butyl ester 

Relevant articles and documents

The 2-(triphenylsilyl)ethoxycarbonyl-("Tpseoc"-) group: A new silicon-based, fluoride cleavable oxycarbonyl protecting group highly orthogonal to the Boc-, Fmoc- and Cbz-groups

Starting from 2-(triphenylsilyl)ethanol a new oxycarbonyl protecting group cleavable by fluoride ion induced Peterson-elimination has been developed. Known 2-(triphenylsilyl)ethanol has been prepared from commercially available triphenylvinylsilane by a hydroboration-oxidation sequence using the sterically hindered borane reagent 9-BBN. The silyl alcohol was subsequently transformed into its chloroformate, imidazolylcarboxylic acid ester and p-nitrophenyl carbonate and used in standard protocols for the formation of carbamates and carbonates. The Tpseoc group proved to be highly resistant against acidic conditions applied in removal of tert-butyl esters and the t-Boc-group. It also withstood catalytic hydrogenation, treatment with morpholine, methylhydrazine and Pd-reagents/allyl-scavanger combinations, conditions required to cleave Cbz-, Fmoc-, phthalimide- and Alloc-groups. The Tpseoc-group is cleaved upon treatment with TBAF/CsF at 0 °C or r.t. with cleavage times reaching from 10 min. to 24 h. Its orthogonality, ease of cleavage and UV-detectability makes the Tpseoc-group a promising alternative to other widely used silicon based amine protecting groups like the Teoc- and SES-groups.