Ajulemic acid, IP-751, DMH-THC-11-OIC, CT-3
(6aR,10aR)-1-羟基-6,6-二甲基-3-(2-甲基辛-2-基)-6a,7,10,10a-四氢苯并[c]色原烯-9-羧酸Chemical Name: (6aR,10aR)-3-(1,1-Dimethylheptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid; (6aR,10aR)-3-(1,1-Dimethylheptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-9-carboxylic acid; 1',1'-Dimethylheptyl-DELTA8-tetrahydrocannabinol-11-oic acid
CAS No. 137945-48-3
项目整合开发状态: Phase II
项目研究机构: Indevus (Licensee), Manhattan Pharmaceuticals (Licensee)
合成路线:The known tetrahydrocannabinol analogue (I) was protected as the silyl ether (II) upon treatment with tert-butyldimethylsilyl chloride and imidazole.Reductive cleavage of the pivaloyl group of (II) by means of LiAlH4 afforded the free allylic alcohol (III).Oxidation with chromic oxide in pyridine led to the aldehyde (IV),which was further oxidized to the acid (V) with sodium chlorite.Finally,removal of the silyl protecting group of (V) employing tetrabutylammonium fluoride furnished the title compound.
📌 参考资料/链接：
参考文献标题:(3R,4R)-DELTA6-Tetrahydrocannabinol-7-oic acids
文献作者:Mechoulam,R.; Burstein,S.H.
参考来源:US 5338753; WO 9401429
📄 详细内容
合成路线:The known tetrahydrocannabinol analogue (I) was protected as the silyl ether (II) upon treatment with tert-butyldimethylsilyl chloride and imidazole.Reductive cleavage of the pivaloyl group of (II) by means of LiAlH4 afforded the free allylic alcohol (III).Oxidation with chromic oxide in pyridine led to the aldehyde (IV),which was further oxidized to the acid (V) with sodium chlorite.Finally,removal of the silyl protecting group of (V) employing tetrabutylammonium fluoride furnished the title compound.
参考文献标题:Synthetic nonpsychotropic cannabinoids with potent antiinflammatory,analgesic,and leukocyte antiadhesion activities
文献作者:Burnstein,S.H.; Audette,C.A.; Breuer,A.; Devane,W.A.; Colodner,S.; Doyle,S.A.; Mechoulam,R.
参考来源:J Med Chem 1992,35(17),3135
合成路线:The aromatic portion of the molecule is generated by the condensation of 1,6-dimethoxyphenol with 1,1-dimethylheptanol in the presence of methanesulfonic acid at 50 C.The crude product is then esterified with diethyl phosphite and triethylamine with cooling to yield the diethyl phosphate derivative.Reduction with lithium in liquid ammonia produces 1-(1',1'-dimethylheptyl)-3,5-hydroxybenzene (I) which is processed crude to the next step.This involves the condensation of the p-menthenediol (II) with the dimethylheptyl resorcinol (I) catalyzed by p-toluenesulfonic acid to give the dimethylheptyl analog of DELTA8-THC (III).Following acetylation of the phenolic group,the allylic methyl group is oxidized to the aldehyde (IV) using selenium dioxide.Further oxidation to the carboxylic acid is accomplished by the use of sodium chlorite.Finally,ajulemic acid is obtained by removal of the acetyl group with sodium carbonate in aqueous methanol.
参考文献标题:Ajulemic Acid
文献作者:Burnstein,S.
参考来源:Drugs Fut 2001,26(4),342
产品链接: CAS No. 137945-48-3››