benzyl (2R)-3-hydroxy-2-(tritylamino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】63275

【品名】benzyl (2R)-3-hydroxy-2-(tritylamino)propanoate

【CA登记号】

【分子式】C₂₉H₂₇NO₃

【分子量】437.53832

【元素组成】C 79.61% H 6.22% N 3.2% O 10.97%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(X)

Treatment of N-trityl-D-serine benzyl ester (X) with I2/PPh3 gives rise to the iodoalanine derivative (XI). Thiol (IX) is then alkylated by iodide (XI) in the presence of Cs2CO3 to furnish thioether (XII). Simultaneous cleavage from the resin and removal of the N-trityl group in (XII) employing trifluoroacetic acid leads to the linear pentapeptide derivative (XIII). This is then cyclized to (XIV) in the presence of DPPA and NaHCO3 in dilute DMF solution. The Cbz and benzyl protecting groups of (XIV) are finally removed by HBr in AcOH to provide the title compound.

参考文献中间体

合成目标

【1】 Rew, Y.; Malkmus, S.; Svensson, C.; Yaksh, T.L.; Chung, N.N.; Schiller, P.W.; Cassel, J.A.; DeHaven, R.; Goodman, M.; Synthesis and biological activities of cyclic lanthionine enkephalin analogues: delta-Opioid receptor selective ligands. J Med Chem 2002, 45, 17, 3746.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IX)	63274	(5S,8S,14S)-14-benzyl-5-[4-(benzyloxy)benzyl]-8-(1-methyl-1-sulfanylethyl)-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid	C₄₀H₄₄N₄O₈S	详情	详情
(X)	63275	benzyl (2R)-3-hydroxy-2-(tritylamino)propanoate	C₂₉H₂₇NO₃	详情	详情
(XI)	63276	benzyl (2S)-3-iodo-2-(tritylamino)propanoate	C₂₉H₂₆INO₂	详情	详情
(XII)	63277	(5S,8S,14S)-14-benzyl-5-[4-(benzyloxy)benzyl]-8-(1-{[(2S)-3-(benzyloxy)-3-oxo-2-(tritylamino)propyl]sulfanyl}-1-methylethyl)-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid	C₆₉H₆₉N₅O₁₀S	详情	详情
(XIII)	63278	(5S,8S,14S)-8-(1-{[(2S)-2-amino-3-(benzyloxy)-3-oxopropyl]sulfanyl}-1-methylethyl)-14-benzyl-5-[4-(benzyloxy)benzyl]-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid	C₅₀H₅₅N₅O₁₀S	详情	详情
(XIV)	63279	benzyl (3S,6S,12S)-6-benzyl-12-({(2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)phenyl]propanoyl}amino)-13,13-dimethyl-5,8,11-trioxo-1-thia-4,7,10-triazacyclotridecane-3-carboxylate	C₅₀H₅₃N₅O₉S	详情	详情

Extended Information