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【结 构 式】 
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【分子编号】36389 【品名】[(1S,12S,13R)-7-amino-14-oxa-11-thia-2,4,6,9-tetraazatetracyclo[10.2.1.0(2,10).0(3,8)]pentadeca-3,5,7,9-tetraen-13-yl]methanol 【CA登记号】 |
【 分 子 式 】C10H11N5O2S 【 分 子 量 】265.29584 【元素组成】C 45.27% H 4.18% N 26.4% O 12.06% S 12.09% |
合成路线1
该中间体在本合成路线中的序号：(XII)The bromination of 2'-deoxyadenosine (VIII) with Br2 in dioxane - water by means of CaCO3 or sodium acetate gives 8-bromo-2'-deoxyadenosine (IX), which by reaction with triphenylmethyl chloride in pyridine - DMF is converted into 8-bromo-2'-deoxy-5'-O-triphenylmethyladenosine (X). The reaction of (X) with p-toluenesulfonyl chloride in pyridine affords 8-bromo-5'-O-triphenylmethyl-3'-O-(p-toluenesulfonyl)-2'-deoxyadenosine (XI), which by reaction with thiourea (A) in refluxing butanol and treatment with propanol-ammonia-water is converted into 2',3'-dideoxy-8-mercapto-8,3'-anhydroadenosine (XII). Finally, this compound is desulfurized by treatment with Raney-Ni in refluxing water.
| 【1】 Morio, I.; Masakatsu, K.; Nucleosides and nucleotides. XLIV. Purine cyclonucleosides. 2. Synthesis of cyclonucleosides having 8,3'-O- and -S-anhydro linkage derived from 2'-deoxyadenosine. Chem Pharm Bull 1970, 18, 12, 2441-46. |
| 【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 |
|---|---|---|---|---|---|---|
| (A) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (VIII) | 18061 | (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanol | 958-09-8 | C10H13N5O3 | 详情 | 详情 |
| (IX) | 36386 | (2R,3S,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanol | C10H12BrN5O3 | 详情 | 详情 | |
| (X) | 36387 | (2R,3S,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanol | C29H26BrN5O3 | 详情 | 详情 | |
| (XI) | 36388 | (2R,3S,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-2-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate | C36H32BrN5O5S | 详情 | 详情 | |
| (XII) | 36389 | [(1S,12S,13R)-7-amino-14-oxa-11-thia-2,4,6,9-tetraazatetracyclo[10.2.1.0(2,10).0(3,8)]pentadeca-3,5,7,9-tetraen-13-yl]methanol | C10H11N5O2S | 详情 | 详情 |