新产品编号:1584091
Chemical Name: (5S,7R,8S,9S,10R)-8,9,10-Trihydroxy-7-(hydroxymethyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decan-4-one
项目整合开发状态: Preclinical
项目研究机构: Lajos Kossuth University (Originator)
合成路线:1-Bromo-1-deoxy-beta-D-glucopyranosyl cyanide (II) was obtained by radical bromination of the corresponding glucopyranosyl cyanide (I).Partial hydrolysis of the cyanide group of (II) by means of TiCl4 in aqueous AcOH afforded amide (III).Subsequent ring closure of (III) with AgSCN or KSCN in nitromethane gave the spiro thiohydantoin (IV).The acetate esters of (IV) were finally eliminated using NaOMe in MeOH.
📌 参考资料/链接：
参考文献标题:Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin
文献作者:Osz,E.; Somsak,L.; Szilagyi,L.; Kovacs,L.; Docsa,T.; Toth,B.; Gergely,P.
参考来源:Bioorg Med Chem Lett 1999,9(10),1385
📄 详细内容
合成路线:1-Bromo-1-deoxy-beta-D-glucopyranosyl cyanide (II) was obtained by radical bromination of the corresponding glucopyranosyl cyanide (I).Partial hydrolysis of the cyanide group of (II) by means of TiCl4 in aqueous AcOH afforded amide (III).Subsequent ring closure of (III) with AgSCN or KSCN in nitromethane gave the spiro thiohydantoin (IV).The acetate esters of (IV) were finally eliminated using NaOMe in MeOH.
参考文献标题:Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of D-gluco- and D-xylopyranosyliene-spiro-(thio)hydantoins and N-(D-glucopyranosyl) amides
文献作者:Soms�? L.; Kovacs,L.; Toth,M.; Osz,E.; Szilagyi,L.; Gyorgydeak,Z.; Dinya,Z.; Docsa,T.; Toth,B.; Gergely,P.
参考来源:J Med Chem 2001,44(17),2843