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【结 构 式】

【分子编号】25366

【品名】di(tert-butyl) 1,4,8,11-tetraazacyclotetradecane-1,11-dicarboxylate

【CA登记号】

【 分 子 式 】C20H40N4O4

【 分 子 量 】400.56216

【元素组成】C 59.97% H 10.07% N 13.99% O 15.98%

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:(IIIc)

Protection of tetraazacyclotetradecane (I) with Boc2O, followed flash chromatography, provided the tri-N-Boc derivative (II) and an unseparable mixture of three isomeric di-N-Boc macrocycles (III). Alkylation of this mixture with ethyl 5-bromovalerate gave a mixture of mono- and dialkylated compounds (IV), from which the required isomer (V) was isolated by flash chromatography. Then, condensation of tri-Boc derivative (II) and monoalkylated di-Boc derivative (V) with alpha-alpha'-dibromo-p-xylene (VI) yielded the desired unsymmetrical bis-macrocycle (VII) along with two symmetrical bis-macrocycle dimers. Subsequent hydrolysis of this mixture with NaOH in the presence of a catalytic amount of Triton B, followed by chromatographic separation, provided pure carboxylic acid (VIII). Further coupling of (VIII) with azidothymidine (IX) using benzotriazol-1-yloxy-tris(pyrrolidino) phosphonium hexafluorophosphate (PyBOP), and final acid deprotection of the Boc groups furnished the title compound.

1 Dessolin, J.; Galea, P.; Vlieghe, P.; Chermann, J.-C.; Kraus, J.-L.; New bicyclam-AZT conjugates: Design, synthesis, anti-HIV evaluation, and their interaction with CXCR-4 coreceptor. J Med Chem 1999, 42, 2, 229.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IIIa) 25364 di(tert-butyl) 1,4,8,11-tetraazacyclotetradecane-1,4-dicarboxylate C20H40N4O4 详情 详情
(IIIb) 25365 di(tert-butyl) 1,4,8,11-tetraazacyclotetradecane-1,8-dicarboxylate C20H40N4O4 详情 详情
(IIIc) 25366 di(tert-butyl) 1,4,8,11-tetraazacyclotetradecane-1,11-dicarboxylate C20H40N4O4 详情 详情
(IVa),(V) 25367 di(tert-butyl) 4-(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,11-dicarboxylate C27H52N4O6 详情 详情
(IVb) 25368 di(tert-butyl) 4-(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,8-dicarboxylate C27H52N4O6 详情 详情
(IVc) 25369 di(tert-butyl) 8-(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,4-dicarboxylate C27H52N4O6 详情 详情
(IVd) 25370 di(tert-butyl) 4,8-bis(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,11-dicarboxylate C34H64N4O8 详情 详情
(IVe) 25371 di(tert-butyl) 4,11-bis(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,8-dicarboxylate C34H64N4O8 详情 详情
(IVf) 25372 di(tert-butyl) 8,11-bis(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecane-1,4-dicarboxylate C34H64N4O8 详情 详情
(I) 25362 1,4,8,11-Tetraazacyclotetradecane 295-37-4 C10H24N4 详情 详情
(II) 25363 tri(tert-butyl) 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate C25H48N4O6 详情 详情
(VI) 18697 1,4-bis(bromomethyl)benzene 623-24-5 C8H8Br2 详情 详情
(VII) 25373 tri(tert-butyl) 11-(4-[[4,8-bis(tert-butoxycarbonyl)-11-(5-ethoxy-5-oxopentyl)-1,4,8,11-tetraazacyclotetradecan-1-yl]methyl]benzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate C60H106N8O12 详情 详情
(VIII) 25374 5-[4,8-bis(tert-butoxycarbonyl)-11-(4-[[4,8,11-tris(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecan-1-yl]methyl]benzyl)-1,4,8,11-tetraazacyclotetradecan-1-yl]pentanoic acid C58H102N8O12 详情 详情
(IX) 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
Extended Information