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【结 构 式】

【分子编号】32180

【品名】(1aS,2aS,2bS,4aS,5aR,6aS,6bR,8aS,9aS)-2a,4a-dimethylhexadecahydro-4bH-oxireno[2'',3'':4',5']cyclopenta[1',2':7,8]phenanthro[2,3-b]oxiren-4-yl acetate

【CA登记号】

【 分 子 式 】C21H30O4

【 分 子 量 】346.4668

【元素组成】C 72.8% H 8.73% O 18.47%

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:(III)

The enol acylation of 5alpha-androst-2-en-17-one (I) with isopropenyl acetate (A) using H2SO4 as catalyst gives 17-acetoxyandrost-2,16-diene (II), which is epoxidized by treatment with m-chloroperbenzoic acid in ether yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (III). The hydrolytic rearrangement of (III) with KOH affords 2alpha,3alpha-epoxy-5alpha-androstan-17beta-ol-16-one (IV), which is condensed with refluxing aqueous piperidine (B) to give 2beta,16beta-dipiperidino-5alpha-androstan-3alpha-ol-17-one (V). The reduction of (V) with NaBH4 in methylene chloride - methanol yields 2beta,16beta-dipiperidino-5alpha-androstan-3alpha,17beta-diol (VI), which is acetylated by reaction with acetyl chloride as usual to afford the corresponding diacetate (VII). Finally, this compound is quaternized by reaction with methyl bromide in ether.

1 Buckett, W.R.; et al.; Pancuronium bromide and other steroidal neuromuscular blocking agents containing acetylcholine fragments. J Med Chem 1973, 16, 10, 1116-24.
2 Serradell, M.N.; Castaner, J.; Blancafort, P.; Hillier, K.; ORG-NC-45. Drugs Fut 1981, 6, 5, 287.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10158 Piperidine 110-89-4 C5H11N 详情 详情
(A) 21178 isopropenyl acetate 108-22-5 C5H8O2 详情 详情
(I) 32178 (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-1,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H28O 详情 详情
(II) 32179 (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate C21H30O2 详情 详情
(III) 32180 (1aS,2aS,2bS,4aS,5aR,6aS,6bR,8aS,9aS)-2a,4a-dimethylhexadecahydro-4bH-oxireno[2'',3'':4',5']cyclopenta[1',2':7,8]phenanthro[2,3-b]oxiren-4-yl acetate C21H30O4 详情 详情
(IV) 32181 (1R,3aS,3bR,5aS,6aS,7aS,8aS,8bS,10aS)-1-hydroxy-8a,10a-dimethylhexadecahydro-2H-cyclopenta[7,8]phenanthro[2,3-b]oxiren-2-one C19H28O3 详情 详情
(V) 16465 (2S,3S,5S,8R,9S,10S,13S,14S,16S)-3-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-17H-cyclopenta[a]phenanthren-17-one C29H48N2O2 详情 详情
(VI) 32182 (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol C29H50N2O2 详情 详情
(VII) 32183 (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-(acetoxy)-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C33H54N2O4 详情 详情
Extended Information