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【结 构 式】 
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【药物名称】 【化学名称】(1alpha,3beta,5Z,7E,23R)-24,24-Difluoro-9,10-secocholesta-5,7,10(19)-triene-1,3,23,25-tetraol 【CA登记号】183274-07-9 【 分 子 式 】C27H42F2O4 【 分 子 量 】468.63019 |
【开发单位】NOF (Originator) 【药理作用】ONCOLYTIC DRUGS, Vitamin D Analogs |
合成路线1
Aldehyde (I), derived from vitamin D2, was submitted to a Reformatsky reaction with ethyl bromodifluoroacetate and activated Zn to produce a mixture of diastereomeric b-hydroxyesters (II). After chromatographic separation, the required (23S)-isomer was condensed with MeMgBr to give tertiary alcohol (III). Finally, desilylation of (III) with tetra n-butylammonium fluoride in THF provided the title compound.
| 【1】 Iwasaki, H.; Miyamoto, Y.; Hosotani, R.; Nakano, Y.; Konno, K.; Takayama, H.; Synthesis and biological evaluation of (23R)- and (23S)-24,24-difluoro-1alpha,23,25-trihydroxyvitamin D3. Chem Pharm Bull 1998, 46, 12, 1932. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40673 | ethyl 2-bromo-2,2-difluoroacetate; Ethylbromodifluoroacetate; 2-bromo-2,2-difluoroacetic acid ethyl ester; bromodifluoroacetic acid ethyl ester | 667-27-6 | C4H5BrF2O2 | 详情 | 详情 | |
| (I) | 25263 | (3R)-3-[(1R,3aR,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]butanal | C35H62O3Si2 | 详情 | 详情 | |
| (II) | 25264 | ethyl (5R)-5-[(1R,3aR,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-2,2-difluoro-3-hydroxyhexanoate | C39H68F2O5Si2 | 详情 | 详情 | |
| (III) | 25321 | (4R,6R)-6-[(1R,3aR,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-3,3-difluoro-2-methyl-2,4-heptanediol | C39H70F2O4Si2 | 详情 | 详情 |
Extended Information