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【结 构 式】 
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【分子编号】45409 【品名】N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-4-methylbenzenesulfonamide 【CA登记号】 |
【 分 子 式 】C13H17NO3S 【 分 子 量 】267.34892 【元素组成】C 58.4% H 6.41% N 5.24% O 17.95% S 11.99% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of cyclopentadiene (I) with tosyl cyanide in acidic water gives the racemic bicyclic lactam (II), which is opened by means of TsCl and NaH to yield cis-3-(tosylamino)-4-cyclopentene-1-carboxylic acid (III). The reduction of (III) with NaBH4 affords the corresponding carbinol (IV), which is acylated with Ac2O and pyridine to provide the acetate (V). The reaction of (V) with Ts-Cl and NaH yields the ditosylamino derivative (VI), which is condensed with 2-amino-6-chloropurine (VII) by means of a Pd catalyst, affording the carbocyclic purine (VIII). Finally, this compound is hydrolyzed with hot aqueous NaOH to give the target carbocyclic guanine.
| 【1】 Jung, M.E.; Rhee, H.; pi-Allylpalladium formation from allylic amines via N,N-ditosylimides and N-tosylamides: Efficient synthesis of the antiviral agent carbovir. J Org Chem 1994, 59, 17, 4719. |
| 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) | 11183 | 1,3-Cyclopentadiene | C5H6 | 详情 | 详情 | |
| (II) | 33410 | cis-2-azabicyclo[2.2.1]hept-5-en-3-one | C6H7NO | 详情 | 详情 | |
| (III) | 45408 | (1S,4R)-4-[[(4-methylphenyl)sulfonyl]amino]-2-cyclopentene-1-carboxylic acid | C13H15NO4S | 详情 | 详情 | |
| (IV) | 45409 | N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-4-methylbenzenesulfonamide | C13H17NO3S | 详情 | 详情 | |
| (V) | 45410 | ((1S,4R)-4-[[(4-methylphenyl)sulfonyl]amino]-2-cyclopenten-1-yl)methyl acetate | C15H19NO4S | 详情 | 详情 | |
| (VI) | 45411 | ((1S,4R)-4-[bis[(4-methylphenyl)sulfonyl]amino]-2-cyclopenten-1-yl)methyl acetate | C22H25NO6S2 | 详情 | 详情 | |
| (VII) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (VIII) | 45398 | [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl methyl carbonate | C13H14ClN5O3 | 详情 | 详情 |