Synthesis of Protected Tetrapeptide, N-o-Ns-N(Me)-Val-N(Me)-Val-N(Me)-Val-N(Me)-Phe-O~tBu

• 作 者: 陈宏亮 冯亚青 孟舒献 刘新刚
• 机 构: School of Chemical Engineering and Technology Tianjin University,School of Chemical Engineering and
• 出 处: Transactions of Tianjin University
• 发表日期: 2006年05期
• 关键词: saturated silica acetate concentrated steps yellow protective antibacterial drie

The protected tetrapeptide, N-o-Ns-N(Me)-Val-N(Me)-Val-N(Me)-Val- N(Me)-Phe-O~tBu, was prepared from L-valine and L-phenylalanine. Tert-butyl acetate and HClO_4 were used to protect carbonyl group, o-nitrobenzenesulfonyl chloride and triethyl amine were used to protect amino group, and N-alkylation was finished with iodomethane. Then the protected amino acid was turned into acid chloride which was taken as coupling reagent. After 14 steps, such as protection, alkylation, deprotection and coupling, the protected tetrapeptide was obtained with a yield of 26.9~0/_0. The structures of intermediates and target compound were identified with NMR spectra and high resolution mass spectra.

The protected tetrapeptide, No-Ns-N (Me) -Val-N (Me) -Val-N (Me) -Val- N (Me) -Phe-O-tBu, was prepared from L-valine and L-phenylalanine . Tert-butyl acetate and HClO_4 were used to protect carbonyl group, o-nitrobenzenesulfonyl chloride and triethyl amine were used to protect amino group, and N-alkylation was finished with iodomethane. Then the protected amino acid was turned into acid chloride which was taken After 14 steps, such as protection, alkylation, deprotection and coupling, the protected tetrapeptide was obtained with a yield of 26.9-0 / _0. The structures of intermediates and target compounds were identified with NMR spectra and high resolution mass spectra .