新产品编号:478273
Chemical Name: [1R-(1alpha,3abeta,4beta,5alpha,7aalpha)]-2-[5-[5-Cyano-1-methylene-4(Z)-pentenyl]-1-[1(R),5-dimethylhexyl]-7a-methylperhydroinden-4-yl]acetic acid
CAS No. 219579-70-1
项目整合开发状态: Biological Testing
项目研究机构: Georgia Institute of Technology (Originator), Mayo Clinic (Originator), University of Arizona (Originator)
合成路线:Ozonolysis of chloesteryl acetate (I) produced keto acid (II),which was converted to the B-homo-6-oxacholestenone (III) upon treatment with SOCl2.Subsequent displacement of the 3beta-acetate group of (III) by NaN3 afforded azide (IV).Pyrolysis of (IV) over silica gel at 180 C yielded a mixture of cleavage products,from which the title nitrile was isolated by column chromatography.
合成路线:Ozonolysis of chloesteryl acetate (I) produced keto acid (II),which was converted to the B-homo-6-oxacholestenone (III) upon treatment with SOCl2.Subsequent displacement of the 3-beta-acetate group of (III) by NaN3 afforded azide (IV).Pyrolysis of (IV) over silica gel at 180 C yielded a mixture of cleavage products,from which the required nitrile (V) was isolated by column chromatography.Finally,selective hydrogenation of the conjugated double bond using Pd/C furnished the title compound.
📌 参考资料/链接：
参考文献标题:Seco-cholestane derivs.and methods of making the same
文献作者:Peng,H.; Zalkow,L.H.(Georgia Technology Research Corp.)
参考来源:US 6011058
📄 详细内容
合成路线:Ozonolysis of chloesteryl acetate (I) produced keto acid (II),which was converted to the B-homo-6-oxacholestenone (III) upon treatment with SOCl2.Subsequent displacement of the 3beta-acetate group of (III) by NaN3 afforded azide (IV).Pyrolysis of (IV) over silica gel at 180 C yielded a mixture of cleavage products,from which the title nitrile was isolated by column chromatography.
合成路线:Ozonolysis of chloesteryl acetate (I) produced keto acid (II),which was converted to the B-homo-6-oxacholestenone (III) upon treatment with SOCl2.Subsequent displacement of the 3-beta-acetate group of (III) by NaN3 afforded azide (IV).Pyrolysis of (IV) over silica gel at 180 C yielded a mixture of cleavage products,from which the title nitrile was isolated by column chromatography.
合成路线:Ozonolysis of chloesteryl acetate (I) produced keto acid (II),which was converted to the B-homo-6-oxacholestenone (III) upon treatment with SOCl2.Subsequent displacement of the 3-beta-acetate group of (III) by NaN3 afforded azide (IV).Pyrolysis of (IV) over silica gel at 180 C yielded a mixture of cleavage products,from which the required nitrile (V) was isolated by column chromatography.Finally,selective hydrogenation of the conjugated double bond using Pd/C furnished the title compound.
参考文献标题:Novel CDC25A phosphatase inhibitors from pyrolysis of 3-alpha-azido-B-homo-6-oxa-4-cholesten-7-one on silica gel
文献作者:Peng,H.; Zalkow,L.H.; Abraham,R.T.; Powis,G.
参考来源:J Med Chem 1998,41(24),4677