(2R,3R,4S)-2-[6-amino-2-(benzylsulfanyl)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol -Drug Synthesis Database

【结构式】

【分子编号】44894

【品名】(2R,3R,4S)-2-[6-amino-2-(benzylsulfanyl)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol

【CA登记号】

【分子式】C₁₇H₁₉N₅O₄S

【分子量】389.43516

【元素组成】C 52.43% H 4.92% N 17.98% O 16.43% S 8.23%

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：(VII)

Treatment of adenosine (I) with H2O2 and HOAc affords N-oxide (II), which is converted into the benzyloxime (IV) via N-benzyloxyadenosine perchlorate (III). Treatment of (IV) with CS2 and NaOH in MeOH followed by separation by filtration and chromatography yields 2-thioadenosine (V), which is then converted into the sodium thiolate salt by treatment with NaOH in MeOH and condensed with benzylbromide (VI) in DMF, providing derivative (VII). Finally, conversion of (VII) into the target compound is achieved by following these steps: (i) treatment of (VII) with thiophosphoryl chloride (PSCl3) in pyridine; (ii) addition of a mixture of Bu3N and (Bu3NH+)2P2O7H2 in DMF; and (iii) treatment with TEAB and chromatographic separation of regioisomers.

参考文献中间体

合成目标

【1】 Kikugawa, K.; et al.; Platelet aggregation inhibitors. IX. Chemical transformation of adenosine into 2-thioadenosine derivatives. Chem Pharm Bull 1977, 25, 8, 1959.
【2】 Fischer, B.; Chulkin, A.; Boyer, J.L.; Gendron, F.-P.; Chapal, J.; Petit, P.; Hillaire-Buys, D.; Harden, K.T.; Beaudoin, A.R.; 2-Thiother 5'-O-(1-thiotriphosphate)adenosine derivatives as new insulin secretagogues acting through P2Y-receptors. J Med Chem 1999, 42, 18, 3636.

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)	44895	(2R,3R,4S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol		C₁₀H₁₃N₅O₄	详情	详情
(II)	44891	6-amino-9-[(2R,3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-1-ium-1-olate		C₁₀H₁₃N₅O₅	详情	详情
(III)	44892	6-amino-1-(benzyloxy)-9-[(2R,3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-1-ium perchlorate		C₁₇H₂₀ClN₅O₉	详情	详情
(IV)	44893	5-amino-N'-(benzyloxy)-1-[(2R,3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1H-imidazole-4-carboximidamide		C₁₆H₂₁N₅O₅	详情	详情
(V)	44896	(2R,3R,4S)-2-(6-amino-2-sulfanyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol		C₁₀H₁₃N₅O₄S	详情	详情
(VI)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(VII)	44894	(2R,3R,4S)-2-[6-amino-2-(benzylsulfanyl)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol		C₁₇H₁₉N₅O₄S	详情	详情

Extended Information