|
【结 构 式】 
|
【分子编号】10242 【品名】(2R)-2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(E)-(trimethylsilyl)methylidene]cyclohexyl]propionic acid 【CA登记号】 |
【 分 子 式 】C23H42O4Si 【 分 子 量 】410.66958 【元素组成】C 67.27% H 10.31% O 15.58% Si 6.84% |
合成路线1
该中间体在本合成路线中的序号：(II)A synthesis of trideuterated artemisin has been published: The methylation of the ketal acid (I) with lithium diisopropylamide and CD3I in THF gives the methylated intermediate (II), which is then submitted to an oxidative cyclization with ozone in dichloromethane. The key intermediate (I) had already been obtained as an intermediate of a previously published total synthesis of artemisin (Avery, M.A. et al. J Amer Chem Soc 1992, 114: 974).
| 【1】 Bonk, J.D.; Avery, M.A.; Mehrotra, S.; Deuterated antimalarials: Synthesis of trideutero-artemisinin, dihydroartemisinin, and arteether. J Label Compd Radiopharm 1996, 38, 8, 249. |
| 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) | 10241 | 2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(Z)-(trimethylsilyl)methylidene]cyclohexyl]acetic acid | C22H40O4Si | 详情 | 详情 | |
| (II) | 10242 | (2R)-2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(E)-(trimethylsilyl)methylidene]cyclohexyl]propionic acid | C23H42O4Si | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)A synthesis of [14C]-labeled artemisin has been reported: The methylation of the ketal acid (I) with lithium diisopropylamide and [14C]-MeI in THF gives the methylated intermediate (II), which is then submitted to an oxidative cyclization with ozone in dichloromethane. The key intermediate (I) had already been obtained as an intermediate of a previously published total synthesis of artemisin (Avery, M.A. et al. J Amer Chem Soc 1992, 114: 974).
| 【1】 Avery, M.A.; Bonk, J.D.; Bupp, J.; Radiolabeled antimalarials: Synthesis of C-14-artemisinin. J Label Compd Radiopharm 1996, 38, 3, 263. |
| 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) | 10241 | 2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(Z)-(trimethylsilyl)methylidene]cyclohexyl]acetic acid | C22H40O4Si | 详情 | 详情 | |
| (II) | 10242 | (2R)-2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(E)-(trimethylsilyl)methylidene]cyclohexyl]propionic acid | C23H42O4Si | 详情 | 详情 | |
| (II) | 10244 | (2R)-2-[(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-[(E)-(trimethylsilyl)methylidene]cyclohexyl]propionic acid | C23H42O4Si | 详情 | 详情 |