(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexanol -Drug Synthesis Database

【结构式】

【分子编号】34605

【品名】(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexanol

【CA登记号】

【分子式】C₂₈H₄₄O

【分子量】396.65676

【元素组成】C 84.79% H 11.18% O 4.03%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXIX)

By allylic oxidation of vitamin D2 (XXIII) with SeO2 and tert-butyl hydroperoxide in pyridine followed by purification by TLC over silicagel. The allylic oxidation of trans-vitamin D2 (XXIX) with SeO2, tert-butyl hydroperoxide and octahydroacridine in dichloromethane gives the trans-1alpha-hydroxyvitamin D2 (XXX), which is isomerized to the target compound by irradiation with UV light with anthracene as photosensitizer.

参考文献中间体

合成目标

【1】 Schnoes, H.K.; Paaren, H.E.; DeLuca, H.F.; Hamer, D.E. (Wisconsin Alumni Research Foundation); Process for preparing 1-hydroxylated vitamin D cpds. from 5,6-trans-vitamin D cpds.. US 4265822 .
【2】 DeLuca, H.F.; Hamer, D.E.; Paaren, H.E.; Schnoes, H.K. (Wisconsin Alumni Research Foundation); Process for preparing 1alpha-hydroxylated cpds.. US 4202829 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXIII)	12425	(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-methylenecyclohexanol	50-14-6	C₂₈H₄₄O	详情	详情
(XXIX)	34605	(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexanol		C₂₈H₄₄O	详情	详情
(XXX)	34602	(1R,3S)-5-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylene-1,3-cyclohexanediol		C₂₈H₄₄O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXIX)

参考文献中间体

合成目标

【1】 Andrews DR, Barton DHR, et aL. 1986.A direct, regio- and stereoselective lα-rhydroxylation of (5E-calciferol derivatives.J Org Chem, 51: 1635~1637

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXIII)	12425	(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-methylenecyclohexanol	50-14-6	C₂₈H₄₄O	详情	详情
(XXVI)	34601	(1S,5R)-3-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-5-[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexanol		C₃₄H₅₈O₂Si	详情	详情
(XXVII)	34604	(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-[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexanol		C₃₄H₅₈O₂Si	详情	详情
(XXIX)	34605	(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexanol		C₂₈H₄₄O	详情	详情
(XXXI)	12428	(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-Methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexyl tert-butyl(dimethyl)silyl ether; [[(1S)-3-((E)-2-[(1R,3aR,7aR)-7a-Methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]octahydro-4H-inden-4-ylidene]ethylidene)-4-methylenecyclohexyl]oxy](tert-butyl)dimethylsilane		C₃₄H₅₈OSi	详情	详情

Extended Information