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【结 构 式】 
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【分子编号】50023 【品名】(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[([(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[(phosphonooxy)methyl]tetrahydro-3-furanyl]oxy)(2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate 【CA登记号】 |
【 分 子 式 】C41H39ClN8O15P2 【 分 子 量 】981.205804 【元素组成】C 50.19% H 4.01% Cl 3.61% N 11.42% O 24.46% P 6.31% |
合成路线1
该中间体在本合成路线中的序号：(IX)The condensation of the cyclic sulfite (I) with N6-benzoyladenine (II) gives the isoadenosine (III), which is condensed with 2-chlorophenylphosphono-bis-triazolide (ClPTr) to yield the phosphate diester (IV). The condensation of (IV) with the deoxycytidine (V) by means of triisopropylbenzenesulfonyl tetrazolide (TPS-TAZ) affords the phosphoric ester (VI), which is treated with dichloroacetic acid (Cl2HOAc) in order to eliminate the dimethoxytrityl protecting group and provide the hydroxymethyl derivative (VII). The phosphorylation of (VII) by means of 2-cyanoethyl phosphate (VIII) gives the protected intermediate (IX), which is finally treated with hot NH4OH to yield the target bis nucleoside phosphate.
| 【1】 Taktakishvili, M.; Nair, V.; Pal, s.; Neamati, N.; Pommier, Y.; Recognition and inhibition of HIV integrase by novel dinucleotides. J Am Chem Soc 2000, 122, 24, 5671. |
| 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) | 50021 | (3aR,4R)-4-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydrofuro[3,4-d][1,3]dioxol-2-one | C27H26O7 | 详情 | 详情 | |
| (II) | 10035 | N-(9H-Purin-6-yl)benzamide; N6-Benzoyladenine | 4005-49-6 | C12H9N5O | 详情 | 详情 |
| (III) | 46816 | N-[9-((3R,4S,5R)-5-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]-4-hydroxytetrahydro-3-furanyl)-9H-purin-6-yl]benzamide | C38H35N5O6 | 详情 | 详情 | |
| (IV) | 46817 | sodium [((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)oxophosphoranolate | C44H38ClN5NaO9P | 详情 | 详情 | |
| (V) | 46818 | (2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-(hydroxymethyl)tetrahydro-3-furanyl acetate | C18H19N3O6 | 详情 | 详情 | |
| (VI) | 46819 | (2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate | C62H56ClN8O14P | 详情 | 详情 | |
| (VII) | 46820 | (2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[[(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-(hydroxymethyl)tetrahydro-3-furanyl]oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate | C41H38ClN8O12P | 详情 | 详情 | |
| (VIII) | 50022 | 2-cyanoethyl dihydrogen phosphate | C3H6NO4P | 详情 | 详情 | |
| (IX) | 50023 | (2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[([(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[(phosphonooxy)methyl]tetrahydro-3-furanyl]oxy)(2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate | C41H39ClN8O15P2 | 详情 | 详情 |