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【结 构 式】 
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【分子编号】38019 【品名】(2R,3R,4S,5R)-2-(6-[[(1S,5S)-5-hydroxy-2-cyclopenten-1-yl]amino]-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol 【CA登记号】 |
【 分 子 式 】C15H19N5O5 【 分 子 量 】349.34656 【元素组成】C 51.57% H 5.48% N 20.05% O 22.9% |
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)The condensation of the ribosyl chloropurine (I) with (rac-trans)-2-amino-3-cyclopentenol (II) by means of NaHCO3 in isopropanol gives a diastereomeric mixture of adenosine derivatives (III) + (IV) that is separated by HPLC. The desired isomer (III) is acetylated with Ac2O and pyridine yielding the tetraacetate (V), which is hydrogenated with tritium over Pt in THF to afford the tetraacetate (VI) of the target compound. Finally, (VI) is deacetylated by means of t-BuNH2 in methanol.
| 【1】 Wadsworth, A.H.; et al.; Synthesis of isotopically labelled versions of adenosine agonist GR79236. J Label Compd Radiopharm 2000, 43, 1, 11. |
| 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) | 18716 | 6-chloropurine riboside; (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | 2004-06-0 | C10H11ClN4O4 | 详情 | 详情 |
| (II) | 38017 | (1S,2S)-2-amino-3-cyclopenten-1-ol | C5H9NO | 详情 | 详情 | |
| (III) | 38019 | (2R,3R,4S,5R)-2-(6-[[(1S,5S)-5-hydroxy-2-cyclopenten-1-yl]amino]-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C15H19N5O5 | 详情 | 详情 | |
| (IV) | 38020 | (2R,3R,4S,5R)-2-(6-[[(1R,5R)-5-hydroxy-2-cyclopenten-1-yl]amino]-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C15H19N5O5 | 详情 | 详情 | |
| (V) | 38021 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(6-[[(1S,5S)-5-hydroxy-2-cyclopenten-1-yl]amino]-9H-purin-9-yl)tetrahydro-3-furanyl acetate | C21H25N5O8 | 详情 | 详情 | |
| (VI) | 38018 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(6-[[(1S,2S)-2-hydroxycyclopentyl]amino]-9H-purin-9-yl)tetrahydro-3-furanyl acetate | C21H27N5O8 | 详情 | 详情 |
Extended Information