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【结 构 式】 
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【分子编号】17487 【品名】methyl 2-[(4R,6S)-2,2-dimethyl-6-[(E)-2-phenylethenyl]-1,3-dioxan-4-yl]acetate 【CA登记号】 |
【 分 子 式 】C17H22O4 【 分 子 量 】290.35928 【元素组成】C 70.32% H 7.64% O 22.04% |
合成路线1
该中间体在本合成路线中的序号：(LXXIV)10) Lactone form: The reduction of 7-phenyl-3,5-dioxo-6(E)-heptenoic acid methyl ester (LXXII) with diethylmethoxyborane and NaBH4 in THF/methanol gives the (3R*,5S*,6E)-dihydroxy ester (LXXIII), which by reaction with acetone dimethylacetal and p-toluenesulfonic acid yields the acetonide (LXXIV). The ozonolysis of (LXXIV) with O3 and dimethylsulfide in methanol affords the aldehyde (LXXV), which is condensed with 2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-ylmethylphosphonic acid diethyl ester (LXXVI) by means of butyllithium to give the acetonide of the methyl ester (LXXVII). Finally, this compound is treated with trifluoroacetic acid to yield the lactone (XLVI). The phosphonate (LXXVI) has been obtained by reaction of the bromomethyl derivative (LXXI) with triethylphosphite (8).
| 【1】 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; NK-104. Drugs Fut 1998, 23, 8, 847-859. |
| 【2】 Yanagawa, E.; Minami, T.; Obara, Y.; Kaiyama, T. (Nissan Chemical Industry, Ltd.; Sagami Chemical Research Center); Condensed pyridines mevalonolactone intermediates and their preparation method. JP 1993310700 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XLVI) | 64696 | (4R,6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl}-4-hydroxytetrahydro-2H-pyran-2-one | C25H22FNO3 | 详情 | 详情 | |
| (LXXI) | 17484 | 3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline | C19H15BrFN | 详情 | 详情 | |
| (LXXII) | 17485 | methyl (E)-3,5-dioxo-7-phenyl-6-heptenoate | C14H14O4 | 详情 | 详情 | |
| (LXXIII) | 17486 | methyl (3R,5S,6E)-3,5-dihydroxy-7-phenyl-6-heptenoate | C14H18O4 | 详情 | 详情 | |
| (LXXIV) | 17487 | methyl 2-[(4R,6S)-2,2-dimethyl-6-[(E)-2-phenylethenyl]-1,3-dioxan-4-yl]acetate | C17H22O4 | 详情 | 详情 | |
| (LXXV) | 17488 | methyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate | C10H16O5 | 详情 | 详情 | |
| (LXXVI) | 17489 | diethyl [2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]methylphosphonate | C23H25FNO3P | 详情 | 详情 | |
| (LXXVII) | 64695 | methyl 2-((4R,6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl}-2,2-dimethyl-1,3-dioxan-4-yl)acetate | C29H30FNO4 | 详情 | 详情 |