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【结 构 式】 
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【分子编号】34596 【品名】(2aR,3aR,3bR,5aR,6R,8aS)-3b,5a-dimethyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2a,3a,3b,3c,4,5,5a,6,7,8,8a,8b-dodecahydro-2H-cyclopenta[7,8]phenanthro[3,4-b]oxiren-2-one 【CA登记号】 |
【 分 子 式 】C28H40O2 【 分 子 量 】408.6244 【元素组成】C 82.3% H 9.87% O 7.83% |
合成路线1
该中间体在本合成路线中的序号：(XX)The Oppenauer oxidation of ergosterol (XIX) gives ergosta-4,6,22-trien-3-one (I), which is dehydrogenated with SeO2 to ergosta-1,4,6,22-tetraen-3-one (II). The epoxidation of (II) with H2O2 and NaOH in dioxane affords the 1alpha,2alpha-epoxide (XX), which is reduced with Li in liquid NH3 to give ergost-5-ene-1alpha,3beta-diol (XXI). The acylation of (XXI) with acetic anhydride and pyridine yields the diacetate (XXII), which is dehydrogenated by the bromination dehydrobromination method to provide the previously reported 1alpha-acetoxyergosteryl acetate (XII). The UV irradiation of (XII) with a high pressure Hg lamp gives the 1alpha-hydroxyvitamin D2 diacetate (XIII), which is finally, deacylated with KOH in methanol.
| 【1】 Lam, H.Y.; et al.; Synthesis of 1alpha-hydroxyergocalciferol. Steroids 1977, 30, 5, 671. |
| 【2】 Schnoes, H.K.; DeLuca, H.F.; Lam, H.-Y. (Wisconsin Alumni Research Foundation); 1alpha-Hydroxyergocalciferol and processes for preparing same. US 3907843 . |
| 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) | 34578 | (10R,13R,14S,17R)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C28H42O | 详情 | 详情 | |
| (II) | 34579 | (10S,13R,14S,17R)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-8,9,10,11,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one | C28H40O | 详情 | 详情 | |
| (XII) | 34588 | (1S,3R,10R,13R,14R,17R)-1-(acetoxy)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C32H48O4 | 详情 | 详情 | |
| (XIII) | 34589 | (1R,5S)-3-((Z)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-5-(acetoxy)-4-methylenecyclohexyl acetate | C32H48O4 | 详情 | 详情 | |
| (XIX) | 34595 | (3S,10R,13R,14R,17R)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | 57-87-4 | C28H44O | 详情 | 详情 |
| (XX) | 34596 | (2aR,3aR,3bR,5aR,6R,8aS)-3b,5a-dimethyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2a,3a,3b,3c,4,5,5a,6,7,8,8a,8b-dodecahydro-2H-cyclopenta[7,8]phenanthro[3,4-b]oxiren-2-one | C28H40O2 | 详情 | 详情 | |
| (XXI) | 34597 | (1S,3R,10R,13R,14S,17R)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol | C28H46O2 | 详情 | 详情 | |
| (XXII) | 34598 | (1S,3R,10R,13R,14S,17R)-1-(acetoxy)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C32H50O4 | 详情 | 详情 |