benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxo-1-(triphenylphosphoranylidene)ethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate -Drug Synthesis Database

【结构式】

【分子编号】39553

【品名】benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxo-1-(triphenylphosphoranylidene)ethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate

【CA登记号】

【分子式】C₆₅H₅₇N₆O₁₀PS

【分子量】1145.241782

【元素组成】C 68.17% H 5.02% N 7.34% O 13.97% P 2.7% S 2.8%

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：(XIV)

The isopropylidene group of (X) is oxidized with ozone affording the corresponding diketonic compound (XI), which is reduced selectively with Zn and acetic acid yielding the hydroxy ketone (XII). The reaction of (XII) with SOCl2 affords the corresponding chloro ketone (XIII), which is treated with triphenylphosphine in a basic medium to give alpha-[3beta-[alpha-(p-benzyloxyphenyl)-alpha-(benzyloxycarbonyl)acetamido]-3alpha-methoxy-4beta-[-3-(1-methyltetrazol-5-yl)thiomethyl-2-oxopropoxy]-2-oxoazetidine-1-yl]-alpha-triphenylphosphoranylideneacetic acid diphenylmethyl ester (XIV). Finally, this compound is treated with refluxing dioxane affording the protected 1-oxa-dethia-3-cephem compound (XV), which is deprotected with trifluoroacetic acid in anisole.

参考文献中间体

合成目标

【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; S-6059. Drugs Fut 1979, 4, 9, 667.
【2】 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(X)	39549	benzhydryl 2-((2R,3R)-3-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)-3-methyl-2-butenoate	C₅₀H₄₈N₆O₁₀S	详情	详情
(XI)	39550	benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxoacetyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate	C₄₇H₄₂N₆O₁₁S	详情	详情
(XII)	39551	benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-1-hydroxy-2-oxoethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate	C₄₇H₄₄N₆O₁₁S	详情	详情
(XIII)	39552	benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-1-chloro-2-oxoethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate	C₄₇H₄₃ClN₆O₁₀S	详情	详情
(XIV)	39553	benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxo-1-(triphenylphosphoranylidene)ethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate	C₆₅H₅₇N₆O₁₀PS	详情	详情
(XV)	38604	benzhydryl (6R,7R)-7-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₄₇H₄₂N₆O₉S	详情	详情

Extended Information