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【结 构 式】

【分子编号】34593

【品名】(1R,3S,5S)-1-((1S)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]-1-methoxyethyl)-2-methylenebicyclo[3.1.0]hex-3-yl acetate

【CA登记号】

【 分 子 式 】C31H48O3

【 分 子 量 】468.72032

【元素组成】C 79.44% H 10.32% O 10.24%

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:(XVII)

The methanolysis of vitamin D2 tosylate (XIV) gives the cyclovitamin (XV), which is oxidized with SeO2 and tert-butyl hydroperoxide in dichloromethane yielding the 1alpha-hydroxy cyclovitamin (XVI). The acylation of (XVI) with acetic anhydride affords the acetate (XVII), which is rearranged with TsOH in hot dioxane to provide 1alpha-acetodyvitamin D2 (XVIII). Finally, this com-pound is hydrolyzed with KOH in aqueous methanol.

1 Paaren, H.E.; et al.; Direct C-1 hydroxylation of vitamin D compounds: Convenient preparation of 1alpha-hydroxyvitamin D3, 1alpha,25-dihydroxyvitamin D3, and 1alpha-hydroxyvitamin D2. Proc Natl Acad Sci USA 1978, 75, 5, 2080.
2 Paaren, H.E.; Hamer, D.E.; DeLuca, H.F.; Schnoes, H.K. (Wisconsin Alumni Research Foundation); Process for preparing 1alpha-hydroxylated cpds.. BE 0873512; US 4195027; WO 7900513 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIV) 34590 (1S)-3-((Z)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexyl 4-methylbenzenesulfonate C35H50O3S 详情 详情
(XV) 34591 (1R,3aR,7aR)-4-[(E,2S)-2-methoxy-2-[(5R)-2-methylenebicyclo[3.1.0]hex-1-yl]ethylidene]-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-1H-indene; (1S)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]-1-[(5R)-2-methylenebicyclo[3.1.0]hex-1-yl]ethyl methyl ether C29H46O 详情 详情
(XVI) 34592 (1R,3S,5S)-1-((1S)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]-1-methoxyethyl)-2-methylenebicyclo[3.1.0]hexan-3-ol C29H46O2 详情 详情
(XVII) 34593 (1R,3S,5S)-1-((1S)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]-1-methoxyethyl)-2-methylenebicyclo[3.1.0]hex-3-yl acetate C31H48O3 详情 详情
(XVIII) 34594 (1S,5R)-3-((Z)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-5-hydroxy-2-methylenecyclohexyl acetate C30H46O3 详情 详情
Extended Information