　 -Drug Synthesis Database

【结构式】

【分子编号】53790

【品名】　

【CA登记号】n/a

【分子式】C₃₁H₄₄O₅

【分子量】496.68736

【元素组成】C 74.96% H 8.93% O 16.11%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(CXII)

In a further synthetic procedure, ketalization of enone (CV) with ethyleneglycol afforded (CVI). After silylation of the primary alcohol group of (CVI) to (CVII), allylic oxidation by means of tert-butyl hydroperoxide and Cr(CO)6 furnished ketone (CVIII). Catalytic hydrogenation of the double bond of (CVIII) to (CIX), followed by ketone reduction with K-Selectride, gave the C-7 alcohol (CX), which was esterified with benzoyl chloride, yielding benzoate ester (CXI). Subsequent desilylation of (CXI) using tetrabutylammonium fluoride provided (CXII).

参考文献中间体

合成目标

【1】 Kinney, W.A.; Meckler, H.; Zhang, X.; Lee, N.; Jones, S.; Rao, M.N.; Bulliard, M. (Genaera Corp.); Stereoselective synthesis of 24-hydroxylated cpds. useful for the preparation of aminosterols, vitamin D analogs, and other cpds.. WO 9824800 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CV)	53783	(8S,9S,10R,13S,14S,17R)-17-[(1S)-2-hydroxy-1-methylethyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one	n/a	C₂₂H₃₄O₂	详情	详情
(CVI)	53784		n/a	C₂₄H₃₈O₃	详情	详情
(CVII)	53785		n/a	C₃₀H₅₂O₃Si	详情	详情
(CVIII)	53786		n/a	C₃₀H₅₀O₄Si	详情	详情
(CIX)	53787		n/a	C₃₀H₅₂O₄Si	详情	详情
(CX)	53788		n/a	C₃₀H₅₄O₄Si	详情	详情
(CXI)	53789		n/a	C₃₇H₅₈O₅Si	详情	详情
(CXII)	53790		n/a	C₃₁H₄₄O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(CXII)

Alcohol (CXII) was converted to aldehyde (CXIII) either by Swern oxidation or by means of NaOCl and TEMPO. The Horner-Emmons condensation of phosphonate (CXV) (prepared from bromo ketone (CXIV) and triethyl phosphite) with aldehyde (CXIII) furnished the unsaturated ketone (CXVI). Asymmetric reduction of the carbonyl group of (CXVI) was accomplished by means of borane-dimethyl sulfide complex in the presence of (S)-MeCBS, yielding (CXVII). Catalytic hydrogenation of the resultant allylic alcohol (CXVII) afforded (CXVIII). The ethylene ketal group of (CXVIII) was then hydrolyzed under acidic conditions to the ketone (CXIX).

参考文献中间体

合成目标

【1】 Zhang, X.; et al.; Synthesis of squalamine utilizing a readily accessible spermidine equivalent. J Org Chem 1998, 63, 23, 8599.
【2】 Kinney, W.A.; Meckler, H.; Zhang, X.; Lee, N.; Jones, S.; Rao, M.N.; Bulliard, M. (Genaera Corp.); Stereoselective synthesis of 24-hydroxylated cpds. useful for the preparation of aminosterols, vitamin D analogs, and other cpds.. WO 9824800 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CXII)	53790		n/a	C₃₁H₄₄O₅	详情	详情
(CXIII)	53791		n/a	C₃₁H₄₂O₅	详情	详情
(CXIV)	53792	1-bromo-3-methyl-2-butanone	19967-55-6	C₅H₉BrO	详情	详情
(CXV)	53793	diethyl 3-methyl-2-oxobutylphosphonate	n/a	C₉H₁₉O₄P	详情	详情
(CXVI)	53794		n/a	C₃₆H₅₀O₅	详情	详情
(CXVII)	53795		n/a	C₃₆H₅₂O₅	详情	详情
(CXVIII)	53796		n/a	C₃₆H₅₄O₅	详情	详情
(CXIX)	53797	(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate	n/a	C₃₄H₅₀O₄	详情	详情

Extended Information