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【结 构 式】 
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【分子编号】33051 【品名】(2R,3S)-2-(azidomethyl)tetrahydro-3-furanol 【CA登记号】 |
【 分 子 式 】C5H9N3O2 【 分 子 量 】143.14548 【元素组成】C 41.95% H 6.34% N 29.35% O 22.35% |
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：(XVII)In an alternative procedure, deoxyribose (XIV) was reduced to 2-deoxy-D-erythropentitol (XV) with NaBH4. Acid-catalyzed cyclization of (XV) produced (IX), which was converted to triflate (XVI) using trifluoromethanesulfonic anhydride and pyridine. Displacement with tetrabutylammonium azide provided azido derivative (XVII). Further treatment with trifluoromethanesulfonic anhydride gave triflate (XVIII), which was then displaced with potassium thioacetate to yield thioester (XII). This was hydrolyzed with NaOMe as above to furnish thiol (XIII).
| 【1】 Lin, Y.-I.; Bitha, P.; Sakya, S.; Strohmeyer, T.W.; Bush, K. (American Cyanamid Co.); Novel 2-thiosubstd. carbapenems. CA 2118961; EP 0617036; JP 1994321948; US 5602118 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 33043 | (2R,3S)-2-(hydroxymethyl)tetrahydro-3-furanol | C5H10O3 | 详情 | 详情 | |
| (XII) | 33046 | S-[(2R,3R)-2-(azidomethyl)tetrahydro-3-furanyl] ethanethioate | C7H11N3O2S | 详情 | 详情 | |
| (XIII) | 33047 | (2R,3R)-2-(azidomethyl)tetrahydro-3-furanthiol; (2R,3R)-2-(azidomethyl)tetrahydro-3-furanylhydrosulfide | C5H9N3OS | 详情 | 详情 | |
| (XIV) | 33048 | (3S,4R)-3,4,5-trihydroxypentanal | 18546-37-7 | C5H10O4 | 详情 | 详情 |
| (XV) | 33049 | (2R,3S)-1,2,3,5-pentanetetrol | C5H12O4 | 详情 | 详情 | |
| (XVI) | 33050 | [(2R,3S)-3-hydroxytetrahydro-2-furanyl]methyl trifluoromethanesulfonate | C6H9F3O5S | 详情 | 详情 | |
| (XVII) | 33051 | (2R,3S)-2-(azidomethyl)tetrahydro-3-furanol | C5H9N3O2 | 详情 | 详情 | |
| (XVIII) | 33052 | (2R,3S)-2-(azidomethyl)tetrahydro-3-furanyl trifluoromethanesulfonate | C6H8F3N3O4S | 详情 | 详情 |
Extended Information