S-16961-1, S-16961
Chemical Name: (R,S)-1,2-O-Bis(hexadecanoyl)-3-O-(3-pyridylcarbonyl)glycerol; (d,l)-1,2-O-Dipalmitoyl-3-O-nicotinoylglycerol
CAS No. 160555-46-4
项目整合开发状态: Phase I
项目研究机构: ADIR (Originator), Servier (Originator)
合成路线:The compound S 16961-1 was synthesized in three steps from solketal (I) by acylation with nicotinoyl chloride (II),deprotection of the isopropylidene ketal (III) by heating in dilute aqueous acetic acid and acylation of this key intermediate (IV) with a slight excess of palmitoyl chloride (V) in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) as catalyst.The enantiomers of S 16961-1 were obtained independently in one step from the commercially available (d)- and (l)-1,2-dipalmitoyl glycerols by acylation with nicotinoyl chloride in the presence of triethylamine.The enantiomers were found equiactive and therefore were not pursued individually.
📌 参考资料/链接：
参考文献标题:Diacylglycerol nicotinates
文献作者:Cordi,A.; Lacoste,J.-M.; Duhault,J.; Espinal,J.; Boulanger,M.(ADIR et Cie.)
参考来源:EP 0574312; JP 1994056786; US 5385920
📄 详细内容
合成路线:The compound S 16961-1 was synthesized in three steps from solketal (I) by acylation with nicotinoyl chloride (II),deprotection of the isopropylidene ketal (III) by heating in dilute aqueous acetic acid and acylation of this key intermediate (IV) with a slight excess of palmitoyl chloride (V) in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) as catalyst.The enantiomers of S 16961-1 were obtained independently in one step from the commercially available (d)- and (l)-1,2-dipalmitoyl glycerols by acylation with nicotinoyl chloride in the presence of triethylamine.The enantiomers were found equiactive and therefore were not pursued individually.
参考文献标题:S 16961-1
文献作者:Cordi,A.A.; Duhault,J.; Laudignon,N.; Castagne,I.
参考来源:Drugs Fut 1996,21(5),490
合成路线:The compound S 16961-1 was synthesized in three steps from solketal (I) by acylation with nicotinoyl chloride (II),deprotection of the isopropylidene ketal (III) by heating in dilute aqueous acetic acid and acylation of this key intermediate (IV) with a slight excess of palmitoyl chloride (V) in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) as catalyst.The enantiomers of S 16961-1 were obtained independently in one step from the commercially available (d)- and (l)-1,2-dipalmitoyl glycerols by acylation with nicotinoyl chloride in the presence of triethylamine.The enantiomers were found equiactive and therefore were not pursued individually.
参考文献标题:Regression of coronary artery disease as a result of intensive lipid lowering therapy in men with high level of apolipoprotein B
文献作者:Brown,G.; Albers,J.J.; Fisher,L.D.; Schaeffer,S.; Lin,J.; Kaplan,C.; Zhao,X.; Bisson,B.; Fitzpatrick,V.; Dodge,H.
参考来源:New Engl J Med 1990,323(19),1289-98