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【结 构 式】

【分子编号】52077

【品名】(E)-3-[3-methoxy-4-[(trimethylsilyl)oxy]phenyl]-2-propenoic acid

【CA登记号】

【 分 子 式 】C13H18O4Si

【 分 子 量 】266.36902

【元素组成】C 58.62% H 6.81% O 24.03% Si 10.54%

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:(IX)

Vanillin (I) was protected as the tetrahydropyranyl ether (II) by treatment with dihydropyran in the presence of pyridinium p-toluenesulfonate. Similarly, hydroxyacetone (III) was converted to the corresponding tetrahydropyranyl ether (IV). Aldol condensation between aldehyde (II) and ketone (IV) using LDA in cold THF furnished the hydroxy ketone (V). Removal of the tetrahydropyranyl protecting groups of (V) under acidic conditions caused the dehydration of the beta-hydroxyl group, affording the unsaturated ketone (VI). The phenolic hydroxyl group of (VI) was then protected as the trimethylsilyl ether (VII). After protection of the phenolic hydroxyl group of ferulic acid (VIII) as the silyl ether (IX), coupling between (IX) and (VII) by means of DCC and DMAP provided the silyl-protected ester (X). This was finally desilylated by treatment with HOAc in aqueous THF.

1 Kim, D.S.H.L. (University of Illinois); Pharmaceutical compsns. useful in the prevention and treatment of beta-amyloid protein-induced disease. WO 0130335 .
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) 22701 4-hydroxy-3-methoxybenzaldehyde 121-33-5 C8H8O3 详情 详情
(II) 52071 3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde C13H16O4 详情 详情
(III) 52072 1-hydroxyacetone 116-09-6 C3H6O2 详情 详情
(IV) 52073 1-(tetrahydro-2H-pyran-2-yloxy)acetone C8H14O3 详情 详情
(V) 52074 4-hydroxy-4-[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-1-(tetrahydro-2H-pyran-2-yloxy)-2-butanone C21H30O7 详情 详情
(VI) 52075 (E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one C11H12O4 详情 详情
(VII) 52076 (E)-1-hydroxy-4-[3-methoxy-4-[(trimethylsilyl)oxy]phenyl]-3-buten-2-one C14H20O4Si 详情 详情
(VIII) 48091 (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 1135-24-6 C10H10O4 详情 详情
(IX) 52077 (E)-3-[3-methoxy-4-[(trimethylsilyl)oxy]phenyl]-2-propenoic acid C13H18O4Si 详情 详情
(X) 52078 (E)-4-[3-methoxy-4-[(trimethylsilyl)oxy]phenyl]-2-oxo-3-butenyl (E)-3-[3-methoxy-4-[(trimethylsilyl)oxy]phenyl]-2-propenoate C27H36O7Si2 详情 详情
Extended Information