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【结 构 式】

【分子编号】22300

【品名】6-Chloro-9-(2'-O,3'-O,5'-O-Triacetyl-beta-D-ribofuranosyl)purine-2-diazonium cation

【CA登记号】

【 分 子 式 】C16H18ClN5O7

【 分 子 量 】427.80112

【元素组成】C 44.92% H 4.24% Cl 8.29% N 16.37% O 26.18%

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:(II)

Diazotization of (I) with isoamyl nitrite in the presence of dipropyl disulfide afforded sulfide (III) through the intermediate diazonium salt (II). Further substitution of the chloro atom of (III) for ammonia provided 2-(propylthio)adenosine (IV). The 5'-hydroxyl group of (IV) was then phosphorylated by reaction with phosphoryl chloride in cold triethyl phosphate followed by aqueous work-up. The resulting 5'-monophosphate (V) was treated with carbonyl diimidazole and tri-n-butylamine to produce the phosphoryl imidazole intermediate (VI), which was finally condensed with dichloromethylenebis(phosphonic acid) (X). The target compound was isolated as the tetrasodium salt upon treatment with NaI in methanol-acetone.

1 Ingall, A.H.; Dixon, J.; Bailey, A.; Coombs, M.E.; Cox, D.; McInally, J.I.; Hunt, S.F.; Kindon, N.D.; Teobald, B.J.; Willis, P.A.; Humphries, R.G.; Leff, P.; Clegg, J.A.; Smith, J.A.; Tomlinson, W.; Antagonists of the platelet P2T receptor: A novel approach to antithrombotic therapy. J Med Chem 1999, 42, 2, 213.
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) 22299 (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate C16H18ClN5O7 详情 详情
(II) 22300 6-Chloro-9-(2'-O,3'-O,5'-O-Triacetyl-beta-D-ribofuranosyl)purine-2-diazonium cation C16H18ClN5O7 详情 详情
(III) 22301 (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-[6-chloro-2-(propylsulfanyl)-9H-purin-9-yl]tetrahydro-3-furanyl acetate C19H23ClN4O7S 详情 详情
(IV) 22302 (2R,3R,4S,5R)-2-[6-amino-2-(propylsulfanyl)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol C13H19N5O4S 详情 详情
(V) 22303 [(2R,3S,4R,5R)-5-[6-amino-2-(propylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydro-2-furanyl]methyl dihydrogen phosphate C13H20N5O7PS 详情 详情
(VI) 22304 [(2R,3S,4R,5R)-5-[6-amino-2-(propylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydro-2-furanyl]methyl hydrogen 1H-imidazol-1-ylphosphonate C16H22N7O6PS 详情 详情
(X) 22305 dichloro(phosphono)methylphosphonic acid CH4Cl2O6P2 详情 详情
Extended Information