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【结 构 式】

【分子编号】25318

【品名】methyl 2-[[[((2S,3S,5R)-3-azido-5-[[(propionylamino)carbonyl]amino]tetrahydro-2-furanyl)methoxy](4-bromophenoxy)phosphoryl]amino]propanoate

【CA登记号】

【 分 子 式 】C20H24BrN6O8P

【 分 子 量 】587.323962

【元素组成】C 40.9% H 4.12% Br 13.6% N 14.31% O 21.79% P 5.27%

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:(VI)

Treatment of 4-bromophenol (I) with phosphoryl chloride gave p-bromophenyl phosphoro- dichloridate (II), which was condensed with alanine methyl ester (III) to furnish alaninyl phosphorochloridate (IV). Further coupling of (IV) with 3'-azidothimidine (V) in the presence of N-methylimidazole afforded phosphate (VI). Then, addition of methyl hypobromite, (prepared from bromine and MeOH) provided the title compound as a diastereomeric mixture.

1 D'Cruz, O.; Jan, S.-T.; Shih, M.-J.; Chen, C.-L.; Uckun, F.M.; Venkatachalam, T.K.; Synthesis of dual function (5R,6R)- and (5S,6S)-5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(para-bromophenyl methoxyalaninyl phosphate) as novel spermicidal and anti-HIV agents. Antivir Chem Chemother 1999, 10, 1, 39.
2 Uckun, F.M.; Venkatachalam, T.; D'Cruz, O. (Parker Hughes Institute); AZT derivs. exhibiting spermicidal and anti-viral activity. WO 9948902 .
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) 25313 4-bromophenol 106-41-2 C6H5BrO 详情 详情
(II) 25314 Dichlorophoephoric acid 4-bromophenyl ester C6H4BrCl2O2P 详情 详情
(III) 25315 methyl 2-aminopropanoate; Alanine, methyl ester 7625-53-8 C4H9NO2 详情 详情
(IV) 25316 methyl 2-[[(4-bromophenoxy)(chloro)phosphoryl]amino]propanoate C10H12BrClNO4P 详情 详情
(V) 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
(VI) 25318 methyl 2-[[[((2S,3S,5R)-3-azido-5-[[(propionylamino)carbonyl]amino]tetrahydro-2-furanyl)methoxy](4-bromophenoxy)phosphoryl]amino]propanoate C20H24BrN6O8P 详情 详情
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