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【结 构 式】

【分子编号】44895

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

【CA登记号】

【 分 子 式 】C10H13N5O4

【 分 子 量 】267.24452

【元素组成】C 44.94% H 4.9% N 26.21% O 23.95%

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:(I)

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.

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