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【结 构 式】

【分子编号】35627

【品名】[(2S,3S,5R)-3-azido-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl hydrogen phosphonate

【CA登记号】

【 分 子 式 】C10H14N5O6P

【 分 子 量 】331.225022

【元素组成】C 36.26% H 4.26% N 21.14% O 28.98% P 9.35%

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:(III)

3'-azido-3'-deoxythimidine (II) was phosphitylated with phosphorus trichloride in triethyl phosphate to yield the corresponding hydrogen phosphonate (III). Subsequent coupling of (III) with 1,2-dipalmitoylglycerol (IV) by means of pivaloyl chloride in pyridine produced phosphite ester (V), which was finally oxidized to the title phosphate with ethanolic iodine.

1 Manouilov, K.K.; Fedorov, I.I.; Boudinot, F.D.; White, C.A.; Kotra, L.P.; Schinazi, R.F.; Hong, C.I.; Chu, C.K.; Lymphatic targeting of anti-HIV nucleosides: Distribution of 3'-azido-3'-deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZdU) after administration of dipalmitoylphosphatidyl prodrugs to mice. Antivir Chem Chemother 1995, 6, 4, 230.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 25317 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione 101703-35-9 C10H13N5O4 详情 详情
(III) 35627 [(2S,3S,5R)-3-azido-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl hydrogen phosphonate C10H14N5O6P 详情 详情
(IV) 35628 2-hydroxy-1-[(palmitoyloxy)methyl]ethyl palmitate C35H68O5 详情 详情
(V) 35629 2-[[([(2S,3S,5R)-3-azido-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methoxy)(oxo)phosphoranyl]oxy]-1-[(palmitoyloxy)methyl]ethyl palmitate C45H80N5O10P 详情 详情
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