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【结 构 式】

【分子编号】58413

【品名】diethyl 2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)-2-(3-pyridinylamino)ethylphosphonate

【CA登记号】

【 分 子 式 】C25H41N2O5PSi

【 分 子 量 】508.670282

【元素组成】C 59.03% H 8.12% N 5.51% O 15.73% P 6.09% Si 5.52%

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)

The condensation between 4-hydroxy-3-methoxy-5-methylbenzaldehyde (I) and 3-aminopyridine (II) yields the corresponding benzalimine (III). The phenolic hydroxyl group of (III) is then protected as the silyl ether (IV) by using t-butyldimethylsilyl chloride and imidazole. Condensation of imine (IV) with the lithium derivative of diethyl methylphosphonate (V) affords the beta-amino phosphonate (VI). Finally, desilylation of (VI) with tetrabutylammonium fluoride and acetic acid provides the target phenol.

1 Phan, H.T.; et al.; Synthesis of a new series of compounds with lipoprotein(a)-lowering activity, Part 3: beta-Substituted-beta-amino-ethylphosphonates. Drugs Fut 2002, 27, Suppl. A.
2 Ife, R.J.; Nguyen, L.M.; Bentzen, C.L.; Diep, V.V.; Azoulay, R.; Phan, H.T.; Niesor, E.J. (Ilex Oncology Research-Europe SA); beta-Substd. beta-aminoethyl phosphonates. US 2002111488; WO 0234756 .
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) 43812 1-(6-methoxy-2-naphthyl)-1-ethanone 3900-45-6 C13H12O2 详情 详情
(II) 33327 3-Pyridinylamine; 3-Aminopyridine; 3-Pyridinamine 462-08-8 C5H6N2 详情 详情
(III) 58411 2-methoxy-6-methyl-4-[(3-pyridinylimino)methyl]phenol C14H14N2O2 详情 详情
(IV) 58412 N-[(E)-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)methylidene]-N-(3-pyridinyl)amine; N-[(E)-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)methylidene]-3-pyridinamine C20H28N2O2Si 详情 详情
(V) 38496 diethyl methylphosphonate 683-08-9 C5H13O3P 详情 详情
(VI) 58413 diethyl 2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-5-methylphenyl)-2-(3-pyridinylamino)ethylphosphonate C25H41N2O5PSi 详情 详情
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