OMPT, LXR-1035
9-辛地丙烯酸(9Z)-, 3-[(羟基甲基唲冲基)氧]-2-甲氧丙基酯Chemical Name: 9(Z)-Octadecenoic acid 2-methoxy-3-(thiophosphonooxy)propyl ester
CAS No. 213738-69-3
项目整合开发状态: Preclinical
项目研究机构: LXR Biotechnology (Originator)
合成路线:Silylation of 1-O-benzylglycerol (I) with tert-butyldimethylsilyl chloride afforded the 1,3-diprotected glycerol (II).After methylation of the free secondary hydroxyl of (II) using MeI and NaH to yield (III),its O-benzyl protecting group was cleaved by hydrogenolysis,yielding (IV).Acylation of alcohol (IV) with oleoyl chloride (V) in the presence of pyridine provided the corresponding ester (VI).Desilylation of (VI) to give alcohol (VII) was carried out by treatment with tetrabutylammonium fluoride.Alcohol (VII) was then condensed with (2-cyanoethyl)-N,N,N',N'-tetraisopropylphosphorodiamidite (VIII) in the presence of 3-hydroxypropionitrile and tetrazole,followed by reaction with elemental sulfur to furnish the thiophosphate (IX).Finally,cleavage of the cyanoethyl ester groups with Et3N and bis(trimethylsilyl)acetamide provided the title compound.
📌 参考资料/链接：
参考文献标题:Compsns.containing lysophosphatidic acids which inhibit apoptosis and uses thereof
文献作者:Boyd,E.A.; Umansky,S.R.; Baxter,A.D.; Price,S.; Goddard,J.G.; Picker,D.H.; Wijkmans,J.C.H.M.(Evotec Biosystems AG; LXR Biotechnology Inc.)
参考来源:WO 9947101
📄 详细内容
合成路线:Silylation of 1-O-benzylglycerol (I) with tert-butyldimethylsilyl chloride afforded the 1,3-diprotected glycerol (II).After methylation of the free secondary hydroxyl of (II) using MeI and NaH to yield (III),its O-benzyl protecting group was cleaved by hydrogenolysis,yielding (IV).Acylation of alcohol (IV) with oleoyl chloride (V) in the presence of pyridine provided the corresponding ester (VI).Desilylation of (VI) to give alcohol (VII) was carried out by treatment with tetrabutylammonium fluoride.Alcohol (VII) was then condensed with (2-cyanoethyl)-N,N,N',N'-tetraisopropylphosphorodiamidite (VIII) in the presence of 3-hydroxypropionitrile and tetrazole,followed by reaction with elemental sulfur to furnish the thiophosphate (IX).Finally,cleavage of the cyanoethyl ester groups with Et3N and bis(trimethylsilyl)acetamide provided the title compound.
参考文献标题:Compsns.containing lysophosphatidic acids which inhibit apoptosis and uses thereof
文献作者:Vmansky,S.R.; Goddard,J.G.; Picker,D.H.; Bathurst,I.C.; Bradley,J.D.; Foehr,M.W.(LXR Biotechnology Inc.)
参考来源:WO 9841213
产品链接: CAS No. 213738-69-3››