methyl (2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[5-(4'-[[2,4-dimethyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidin-8(5H)-yl]methyl][1,1'-biphenyl]-2-yl)-2H-1,2,3,4-tetraazol-2-yl]tetrahydro-2H-pyran-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】26026

【品名】methyl (2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[5-(4'-[[2,4-dimethyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidin-8(5H)-yl]methyl][1,1'-biphenyl]-2-yl)-2H-1,2,3,4-tetraazol-2-yl]tetrahydro-2H-pyran-2-carboxylate

【CA登记号】

【分子式】C₃₆H₃₇N₇O₁₀

【分子量】727.73096

【元素组成】C 59.42% H 5.12% N 13.47% O 21.99%

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：(VII)

1) The oxidation of tasosartan (V) with KMnO4 and NaOH in water gives metabolite (I). 2) The condensation of tasosartan (V) with 2,3,4-tri-O-acetyl-1alpha-bromo-1-deoxy-D-glucopyranosyluronic acid methyl ester (VI) by means of KOH in refluxing acetone gives the acetylated glucuronide methyl ester (VII), which is deacetylated with KCN in methanol yielding glucuronide methyl ester (VIII). Finally, this compound is hydrolyzed with NaOH in methanol to afford metabolite (II).

参考文献中间体

合成目标

【1】 Ellingboe, J.W.; Collini, M.D.; Quagliato, D.; Chen, J.; Antane, M.; Schmid, J.; Hartupee, D.; White, V.; Park, C.H.; Tanikella, T.; Bagli, J.F.; Metabolites of the angiotensin II antagonist tasosartan: The importance of a second acidic group. J Med Chem 1998, 41, 22, 4251.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	26023	5-hydroxy-2,4-dimethyl-8-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one	C₂₃H₂₁N₇O₂	详情	详情
(II)	26024	sodium (2S,3S,4S,5R,6R)-6-[5-(4'-[[2,4-dimethyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidin-8(5H)-yl]methyl][1,1'-biphenyl]-2-yl)-2H-1,2,3,4-tetraazol-2-yl]-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate	C₂₉H₂₈N₇NaO₇	详情	详情
(V)	26025	2,4-dimethyl-8-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one	C₂₃H₂₁N₇O	详情	详情
(VI)	17580	methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetoxy)-6-bromotetrahydro-2H-pyran-2-carboxylate	C₁₃H₁₇BrO₉	详情	详情
(VII)	26026	methyl (2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[5-(4'-[[2,4-dimethyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidin-8(5H)-yl]methyl][1,1'-biphenyl]-2-yl)-2H-1,2,3,4-tetraazol-2-yl]tetrahydro-2H-pyran-2-carboxylate	C₃₆H₃₇N₇O₁₀	详情	详情
(VIII)	26027	methyl (2S,3S,4S,5R,6R)-6-[5-(4'-[[2,4-dimethyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidin-8(5H)-yl]methyl][1,1'-biphenyl]-2-yl)-2H-1,2,3,4-tetraazol-2-yl]-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate	C₃₀H₃₁N₇O₇	详情	详情

Extended Information