119255-37-7

Basic information

• Product Name: N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester
• Synonyms: N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester
• CAS NO: 119255-37-7
• Molecular Weight: 501.536
• Mol File: 119255-37-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester(CAS DataBase Reference)
• NIST Chemistry Reference: N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester(119255-37-7)
• EPA Substance Registry System: N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester(119255-37-7)

Safety Data

• Hazardous Substances Data: 119255-37-7(Hazardous Substances Data)

Upstream product

• 7598-10-9 2-(bromomethyl)anthraquinone 
• 3978-80-1 Boc-Tyr-OH 

Downstream Products

• 127103-00-8 N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester 
• 118903-66-5 TFA*H-Tyr(PO₃Me₂)-Val-OMaq 
• 118903-64-3 N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester 
• 92264-99-8 N^α-(tert-butoxycarbonyl)-O-(O',O''-dimethylphosphoro)-L-tyrosine 
• 119255-41-3 (S)-2-tert-Butoxycarbonylamino-3-[4-(hydroxy-phenylsulfanyl-phosphoryloxy)-phenyl]-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester 
• 119255-40-2 O-(S,S-Diphenyl)phosphorodithioyl Boc-tyrosine 
• 119255-38-8 (S)-3-[4-(Bis-phenylsulfanyl-phosphoryloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid 9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl ester 

Relevant articles and documents

Synthesis of O-phosphotyrosine-containing peptides: 3. Synthesis of H-Pro-Try(P)-Val-OH via dimethyl phosphate protection and the use of improved deprotection procedures

The phosphorylated derivative N(α)-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester, Boc-Tyr(PO3Me2)-OMaq (2), was prepared in high yields by either phosphotriester or ''phosphite-triester'' phosphorylation of Boc-Tyr-OMaq (1). In the former case, either sodium hydride or lithium diisopropylamide was used to generate the phenoxide ion which was then treated with dimethyl phosphorochloridate (MeO)2P(O)Cl. Alternatively, dimethyl N,N-diethylphosphoramidite (MeO)2PNEt2 (15) and 1H-tetrazole were used in the phosphite-triester approach, to effect the quantitative, acid-catalyzed phosphitylation followed by m-chloroperoxybenzoic acid oxidation of the phosphite-triester intermediate. Removal of the 2-methylanthraquinone group (Maq) by reduction with sodium dithionite afforded Boc-Tyr(PO3Me2)-OH (3) in 70-75% overall yield. This derivative was used in the solution-phase synthesis of the tripeptide Boc-Pro-Tyr(PO3Me2)-Val-OMaq (9) by the Boc mode of peptide synthesis, which was followed by the removal of the Maq and Boc groups by successive dithionite reduction and 40% CF3CO2H/CH2Cl2 treatments respectively. Six procedures for the cleavage of the methyl phosphate group by acidolysis or silylolysis from H-Pro-Tyr(PO3Me2)-Val-OH·TFA (11) were examined with the source of hard acid being CF3SO3H, (CH3)3SiBr, (CH3)3SiBr, or CF3SO3Si(CH3)3 and either thioanisole or dimethyl sulfide as the soft nucleophile. While deprotection treatments gave H-Pro-Tyr(P)-Val-OH in modest isolated yields, monitoring with 31P NMR and 13C NMR indicated quantitative deprotection. Enhanced rates of methyl cleavage from the protecting phosphate group were observed with the use of thioanisole.