新产品编号:331147
Chemical Name: 5(R)-(Acetylamino)-2(S)-(5-bromo-1H-indol-3-yloxy)-6(R)-[2(R),3-dihydroxy-1(R)-methoxypropyl]-4(S)-methoxytetrahydro-2H-pyran-2-carboxylic acid
CAS No. 203447-96-5
项目整合开发状态: Biological Testing
项目研究机构: ZymeTx (Originator)
合成路线:The methylation of the protected ketoside (I) with dimethyl sulfate and NaH gives the trimethoxy compound (II),which is treated with AcOH to eliminate the cyclic ketal protecting group to yield the dihydroxy compound (III).The hydrolysis of the methyl ketal and the ester group of (III) with NaOH affords the hydroxyacid (IV),which is converted into the chloroester (V) by methylation with TFA/methanol and acetylation and chlorination with acetyl chloride.The condensation of (V) with 1-acetyl-5-bromoindol-2-ol (VI) by means of NaOH gives the adduct (VII),which is deacetylated with sodium methoxide in methanol yielding the dihydroxy ester (VIII).Finally,the ester group of (VIII) is hydrolyzed with NaOH.
📌 参考资料/链接：
参考文献标题:4,7-Dialkoxy N-acetylneuraminic acid derivs.and methods for detection of influenza type A and B viruses in clinical specimens
文献作者:Shimasaki,C.D.; Liav,A.; Hansjergen,J.A.(Oklahoma Medical Research Foundation)
参考来源:US 5719020; WO 9813372
📄 详细内容
合成路线:The methylation of the protected ketoside (I) with dimethyl sulfate and NaH gives the trimethoxy compound (II),which is treated with AcOH to eliminate the cyclic ketal protecting group to yield the dihydroxy compound (III).The hydrolysis of the methyl ketal and the ester group of (III) with NaOH affords the hydroxyacid (IV),which is converted into the chloroester (V) by methylation with TFA/methanol and acetylation and chlorination with acetyl chloride.The condensation of (V) with 1-acetyl-5-bromoindol-2-ol (VI) by means of NaOH gives the adduct (VII),which is deacetylated with sodium methoxide in methanol yielding the dihydroxy ester (VIII).Finally,the ester group of (VIII) is hydrolyzed with NaOH.
参考文献标题:Synthesis of bromoindolyl 4,7-di-O-methyl-Neu5Ac: Specificity toward influenza A and B viruses
文献作者:Liav,A.; Hansjergen,J.A.; Achyuthan,K.E.; Shimasaki,C.D.
参考来源:Carbohydr Res 1999,317(1-4),198