Sitostanol ascorbyl phosphate
Chemical Name: Phosphoric acid [(3beta,5alpha,24R)-stigmastan-3-yl] L-ascorbic acid-2-O-yl diester disodium salt; 2-O-[Hydroxy[(3beta,5alpha,24R)-stigmastan-3-O-yl]phosphoryl]-L-ascorbic acid disodium salt
CAS No. 315179-26-1 (monosodium salt)
项目整合开发状态: Phase II
项目研究机构: Forbes Medi-Tech (Originator)
合成路线:Reaction of campestanol (I) with phosphorus oxychloride and pyridine gives the dichlorophosphoryl compound (II).Ascorbic acid (III) is protected as the 5,6-isopropylidene ketal (IV) upon treatment with acetone and fuming sulfuric acid.Condensation of (IV) with acid chloride (II) provides the phosphoryl monochloride (V),which is hydrolyzed under acidic conditions to yield the phosphate diester (VI).Finally,compound (VI) is converted to the target disodium salt by using an ethanolic solution of NaOMe.(1,2)
合成路线:Reaction of sitostanol (I) with phosphorus oxychloride and pyridine affords the dichlorophosphoryl compound (II).Ascorbic acid (III) is protected as the 5,6-isopropylidene ketal (IV) upon treatment with acetone and fuming sulfuric acid.Condensation of (IV) with acid chloride (II) provides the phosphoryl monochloride (V),which is hydrolyzed under acidic conditions to yield the phosphate diester (VI).Finally,compound (VI) is converted to the target disodium salt by using an ethanolic solution of NaOMe.(1,2)
📌 参考资料/链接：
参考文献标题:Conjugates of phytosterol or phytostanol with ascorbic acid and use thereof in treating or preventing cardiovascular disease
文献作者:Chen,H.; Milanova,R.K.; Kutney,J.P.; Hou,D.; Ding,Y.(Forbes Medi-Tech Inc.)
参考来源:JP 2003522124; WO 0100653
📄 详细内容
合成路线:Reaction of campestanol (I) with phosphorus oxychloride and pyridine gives the dichlorophosphoryl compound (II).Ascorbic acid (III) is protected as the 5,6-isopropylidene ketal (IV) upon treatment with acetone and fuming sulfuric acid.Condensation of (IV) with acid chloride (II) provides the phosphoryl monochloride (V),which is hydrolyzed under acidic conditions to yield the phosphate diester (VI).Finally,compound (VI) is converted to the target disodium salt by using an ethanolic solution of NaOMe.(1,2)
合成路线:Reaction of sitostanol (I) with phosphorus oxychloride and pyridine affords the dichlorophosphoryl compound (II).Ascorbic acid (III) is protected as the 5,6-isopropylidene ketal (IV) upon treatment with acetone and fuming sulfuric acid.Condensation of (IV) with acid chloride (II) provides the phosphoryl monochloride (V),which is hydrolyzed under acidic conditions to yield the phosphate diester (VI).Finally,compound (VI) is converted to the target disodium salt by using an ethanolic solution of NaOMe.(1,2)
参考文献标题:Novel structures comprising phytosterol and/or phytostanol and ascorbic acid and use thereof as weight regulating agents
文献作者:Novak,E.; Milanova,R.K.; Kutney,J.P.; Pritchard,H.P.; Lukic,T.(Forbes Medi-Tech Inc.)
参考来源:WO 0234241