(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 -Drug Synthesis Database

【结构式】

【分子编号】34590

【品名】(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

【CA登记号】

【分子式】C₃₅H₅₀O₃S

【分子量】550.8462

【元素组成】C 76.32% H 9.15% O 8.71% S 5.82%

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：(XIV)

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.

参考文献中间体

合成目标

【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	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