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【结 构 式】 
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【分子编号】36381 【品名】(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C36H33N5O5S 【 分 子 量 】647.75472 【元素组成】C 66.75% H 5.13% N 10.81% O 12.35% S 4.95% |
合成路线1
该中间体在本合成路线中的序号：(II)The elimination reaction of (III) with sodium ethoxide in DMF gives 2',3'-dideoxy-2',3'-didehydroadenosine (V), which is hydrogenated with H2 over Pd/C in ethanol.
| 【1】 McCarthy, J.R.; et al.; Purine nucleosides. XIV. Unsaturated furanosyl adenine nucleosides prepared via base-catalysed elimination reactions of 2'-deoxyadenosine derivatives. J Am Chem Soc 1966, 88, 7, 1549-53. |
| 【2】 Castaner, J.; Hopkins, S.J.; Serradell, M.N.; Blancafort, P.; 2',3'-Dideoxyadenosine. Drugs Fut 1982, 7, 4, 244. |
| 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) | 34204 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol | C29H27N5O3 | 详情 | 详情 | |
| (II) | 36381 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate | C36H33N5O5S | 详情 | 详情 | |
| (III) | 36382 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate | C17H19N5O5S | 详情 | 详情 | |
| (V) | 11994 | [(2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol | 7057-48-9 | C10H11N5O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)The reaction of 5'-triphenylmethyl-2'-deoxyadenosine (I) with p-toluenesulfonyl chloride in pyridine gives 5'-triphenylmethyl-3'-(p-toluenesulfonyl)-2'-deoxyadenosine (II), which by partial hydrolysis with acetic acid yields 3'-p-toluenesulfonyl)-2'-deoxyadenosine (III). The reaction of (III) with ethylmercaptane (A) by means of sodium ethoxide affords 3'-ethylthio-2',3'-dideoxyadenosine (IV), which is finally desulfurized by treatment with Raney-Ni in refluxing methyl cellosolve - ethanol (100 C).
| 【1】 Robins, M.J.; et al.; The synthesis of 2',3'-dideoxyadenosine from 2'-deoxyadenosine. J Am Chem Soc 1964, 86, 17, 3585-86. |
| 【2】 Robins, M.J.; et al.; Purine nucleosides. XII. The preparation of 2',3'-dideoxyadenosine, 2',5'dideoxyadenosine and 2',3',5'-trideoxyadenosine from 2'-deoxyadenosine. Biochem J 1966, 5, 1, 224-231. |
| 【3】 Castaner, J.; Hopkins, S.J.; Serradell, M.N.; Blancafort, P.; 2',3'-Dideoxyadenosine. Drugs Fut 1982, 7, 4, 244. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 23712 | 1-ethanethiol; ethylhydrosulfide | 75-08-1 | C2H6S | 详情 | 详情 |
| (I) | 34204 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol | C29H27N5O3 | 详情 | 详情 | |
| (II) | 36381 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate | C36H33N5O5S | 详情 | 详情 | |
| (III) | 36382 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate | C17H19N5O5S | 详情 | 详情 | |
| (IV) | 36383 | [(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3-(ethylsulfanyl)tetrahydro-2-furanyl]methanol | C12H17N5O2S | 详情 | 详情 |