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【结 构 式】

【分子编号】57567

【品名】4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid

【CA登记号】

【 分 子 式 】C34H33IN2O10

【 分 子 量 】756.54797

【元素组成】C 53.98% H 4.4% I 16.77% N 3.7% O 21.15%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with diethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.

1 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171.
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) 31154 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione 54-42-2 C9H11IN2O5 详情 详情
(II) 57566 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione C30H29IN2O7 详情 详情
(III) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(IV) 57567 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid C34H33IN2O10 详情 详情
(V) 57568 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-[2-(2-hydroxyethoxy)ethyl] succinate C38H41IN2O12 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with triethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.

1 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171.
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) 31154 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione 54-42-2 C9H11IN2O5 详情 详情
(II) 57566 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione C30H29IN2O7 详情 详情
(III) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(IV) 57567 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid C34H33IN2O10 详情 详情
(V) 57569 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl} succinate C40H45IN2O13 详情 详情
Extended Information