2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate -Drug Synthesis Database

【结构式】

【分子编号】45099

【品名】2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate

【CA登记号】

【分子式】C₂₄H₃₄O₆

【分子量】418.53036

【元素组成】C 68.88% H 8.19% O 22.94%

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：(XV)

5) The title product [3H]- or [2H]-labeled at C7 of the steroid nucleus is synthesized starting from 21-acetoxy-11beta,17alpha-dihydroxy-6-methylpregna-4,6-diene-3,20-dione (XII), which is hydrogenated with tritium or deuterium over Pd/C in methanol yielding a mixture of the two isomeric dihydro compounds (XIII) and (XIV). The treatment of this mixture with 6N HCl affords compound (XV) labeled at C7, which is dehydrogenated with SeO2 in refluxing tert-butanol and deacetylated with KOH in methanol, yielding methylprednisolone labeled with 3H or 2H at C7 (XVI). Finally, this compound is condensed with 8-oxo-8-[N-(2-sulfoethyl)-N-methylamino]octanoic acid (III) by means of tert-butoxycarbonyl chloride as before.

参考文献中间体

合成目标

【1】 Stolle, W.T.; Runge, T.A.; Hsi, R.S.P.; Synthesis of carbon-14 and tritium labeled methylprednisolone suleptanate. J Label Compd Radiopharm 1990, 28, 255-80.
【2】 Graul, A.; Leeson, J.; Castaner, J.; Methylprednisolone Suleptanate. Drugs Fut 1997, 22, 8, 833.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	11822	7-[N-Methyl-N-(2-sulfoethyl)carbamoyl]heptanoic acid disodium salt		C₁₁H₁₉NNaO₆S	详情	详情
(XII)	11831	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₂O₆	详情	详情
(XIII)	11832	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XIII)	45093	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XIII)	45094	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XIV)	11833	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XIV)	45095	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XIV)	45096	2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XV)	11834	2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XV)	45099	2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XV)	45100	2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₄H₃₄O₆	详情	详情
(XVI)	10394	Methylprednisolone	83-43-2	C₂₂H₃₀O₅	详情	详情
(XVI)	45097	(6S,8S,9S,10R,11S,13S,14S,17R)-17-glycoloyl-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one		C₂₂H₃₀O₅	详情	详情
(XVI)	45098	(6S,8S,9S,10R,11S,13S,14S,17R)-17-glycoloyl-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one		C₂₂H₃₀O₅	详情	详情

Extended Information