1-[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-propyn-1-ol -Drug Synthesis Database

【结构式】

【分子编号】31058

【品名】1-[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-propyn-1-ol

【CA登记号】

【分子式】C₁₅H₁₇N₅O₄

【分子量】331.33128

【元素组成】C 54.38% H 5.17% N 21.14% O 19.32%

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：(V)

The Grignard condensation of the protected adenosine derivative (I) with trimethylsilylethynyl magnesium bromide (II) in THF gives the diastereomeric mixture (III), which is separated by column chromatography. The desired isomer (IV) is treated with ammonia in methanol to yield the isopropylidene derivative of the target compound (V), which is finally deprotected with 90% aqueous TFA.

参考文献中间体

合成目标

【1】 Matsuda, A.; Saitoh, Y.; Nakata, H.; Minakawa, N.; Yoshimura, Y.; Kosaki, H.; Nucleosides and nucleotides. 177. 9-(6,7-dideoxy-beta-D-allo-hept-5-ynofuranosyl)adenine: A selective and potent ligand for P3 purinoceptor-like protein. J Med Chem 1998, 41, 15, 2676.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	31054	N-[9-[(3aR,4R,6S,6aR)-6-formyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl]benzamide	C₂₀H₁₉N₅O₅	详情	详情
(II)	31055	bromo[2-(trimethylsilyl)ethynyl]magnesium	C₅H₉BrMgSi	详情	详情
(III)	31056	N-(9-[(3aR,4R,6R,6aR)-6-[(1S)-1-hydroxy-3-(trimethylsilyl)-2-propynyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl)benzamide	C₂₅H₂₉N₅O₅Si	详情	详情
(IV)	31057	N-(9-[(3aR,4R,6R,6aR)-6-[1-hydroxy-3-(trimethylsilyl)-2-propynyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl)benzamide	C₂₅H₂₉N₅O₅Si	详情	详情
(V)	31058	1-[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-propyn-1-ol	C₁₅H₁₇N₅O₄	详情	详情

Extended Information