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【结 构 式】

【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
      24,24-Difluoro-1alpha,23(R),25-trihydroxyvitamin D3

【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