methyl (E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoate -Drug Synthesis Database

【结构式】

【分子编号】39957

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

【CA登记号】

【分子式】C₁₇H₂₀O₆

【分子量】320.3422

【元素组成】C 63.74% H 6.29% O 29.97%

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：(XXIX)

The reaction of (XXVI) with HI and red P in acetic acid gives 4-methyl-5,7-dihydroxyphthalide (XXVII), which is condensed with methyl 6-bromo-4-methyl-4-hexenoate (XXVIII) by means of Ag2O in dioxane yielding the methyl ester (XXIX). The monomethylation of (XXIX) with diazomethane in benzene affords the methyl ester of mycophenolic acid (XXX), which is finally hydrolyzed with aqueous NaOH.

参考文献中间体

合成目标

【1】 Castaner, J.; Hillier, K.; Mycophenolic acid. Drugs Fut 1978, 3, 8, 594.
【2】 Canonica, L.; et al.; Total synthesis of mycophenolic acid. Tetrahedron Lett 1971, 28, 2691-92.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVI)	39954	5,7-dimethoxy-4-methyl-2-benzofuran-1(3H)-one	C₁₁H₁₂O₄	详情	详情
(XXVII)	39955	5,7-dihydroxy-4-methyl-2-benzofuran-1(3H)-one	C₉H₈O₄	详情	详情
(XXVIII)	39956	methyl (E)-6-bromo-4-methyl-4-hexenoate	C₈H₁₃BrO₂	详情	详情
(XXIX)	39957	methyl (E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoate	C₁₇H₂₀O₆	详情	详情
(XXX)	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