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【结 构 式】

【分子编号】64490

【品名】(E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoic acid

【CA登记号】

【 分 子 式 】C18H22O6

【 分 子 量 】334.36908

【元素组成】C 64.66% H 6.63% O 28.71%

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)

The cyclization of the 3-oxoglutarate (I) with the alkynal (II) gives the benzoate derivative (III), which is treated with CH3I and NaH to yield the dimethoxy benzoate (IV). The reduction o the formyl group of (IV) by means of NaBH4 affords the hydroxymethyl derivative (V), which is treated with MsCl and TEA to provide the mesylate (VI). The reduction of the mesylate group of (VI) by means of NaBH4 gives the methyl derivative (VII), which is cyclized by means of K2CO3 to yield the isobenzofuranone (VIII). The ozonolysis of the dimethylvinyl group of (VIII) affords the aldehyde (IX), which is oxidized with CrO3 to provide the carboxylic acid (X). The reaction of (X) with diazomethane gives the corresponding methyl ester (XI), which selectively demethylates with BCl3 in CH2Cl2 to yield mycophenolic acid methyl ester (XII). Finally, this compound is hydrolyzed with LiOH to provide the target carboxylic acid.

1 Covarrubias-Zuniga, A.; Gonzalez-Lucas, A.; Dominguez, M.M.; Total synthesis of mycophenolic acid. Tetrahedron 2003, 59, 11, 1989.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 64481 dimethyl 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-3-oxopentanedioate C17H26O5 详情 详情
(II) 64482 4-oxo-2-butynyl pivalate C9H12O3 详情 详情
(III) 64483 methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-5-formyl-2,4-dihydroxybenzoate C25H34O7 详情 详情
(IV) 64484 methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-5-formyl-2,4-dimethoxybenzoate C27H38O7 详情 详情
(V) 64485 methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-5-(hydroxymethyl)-2,4-dimethoxybenzoate C27H40O7 详情 详情
(VI) 64486 methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2,4-dimethoxy-5-{[(methylsulfonyl)oxy]methyl}benzoate C28H42O9S 详情 详情
(VII) 64487 methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2,4-dimethoxy-5-methylbenzoate C27H40O6 详情 详情
(VIII) 64488 6-[(2E)-3,7-dimethyl-2,6-octadienyl]-5,7-dimethoxy-4-methyl-2-benzofuran-1(3H)-one C21H28O4 详情 详情
(IX) 64489 (E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenal C18H22O5 详情 详情
(X) 64490 (E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoic acid C18H22O6 详情 详情
(XI) 64491 methyl (E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoate C19H24O6 详情 详情
(XII) 39958 methyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoate C18H22O6 详情 详情
Extended Information