(2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】23969

【品名】(2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenecarboxylic acid

【CA登记号】

【分子式】C₃₀H₄₈O₃

【分子量】456.70932

【元素组成】C 78.9% H 10.59% O 10.51%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The oxidation of 3-beta-acetoxyolean-12-en-30-oic acid methyl ester (I) with H2O2 in hot acetic acid gives 3beta-acetoxy-12-oxoolean-30-oic acid methyl ester (II), which is treated with Br2 in 40% HBr acetic acid yielding 3beta-acetoxy-12-oxoolean 9-en-30-oic acid methyl ester (III). The reduction of (III) with hydrazine and sodium ethoxide in ethanol affords 3beta-hydroxyolean-9(11)-en-30-oic acid (IV), which is finally esterified with succinic anhydride (V) in hot pyridine.

参考文献中间体

合成目标

【1】 Pifferi, G.; Umani Ronchi, A.; Farina, C.; Gamba, A. (ISF SpA); 3beta-Hydroxy-18beta-olean-9-en-30-oic acids. DE 2811253; FR 2383909; GB 1575494; JP 78116363; US 4173648 .
【2】 Prous, J.; Castaner, J.; Deloxolone sodium. Drugs Fut 1986, 11, 8, 643.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	23967	(2S,4aS,6aR,6bR,8aR,10S,12aR,14bR)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-2-picenyl acetate		C₃₃H₅₂O₄	详情	详情
(II)	23980	(2S,4aS,6aR,6bR,8aR,10S,12aR,14aR,14bS)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-14-oxodocosahydro-2-picenyl acetate		C₃₃H₅₂O₅	详情	详情
(III)	23968	(2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenyl acetate		C₃₃H₅₀O₅	详情	详情
(IV)	23969	(2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenecarboxylic acid		C₃₀H₄₈O₃	详情	详情
(V)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情

Extended Information