新产品编号:286851
Chemical Name: O-[2-Deoxy-2-[3(R)-(tetradecanoyloxy)tetradecanoylamino]-beta-D-glucopyranosyl]-N-(tetradecanoyl)-L-seryl-beta-alanine
CAS No. 197663-09-5
项目整合开发状态: Biological Testing
项目研究机构: University of Shizuoka (Originator)
合成路线:Intermediate (VII) was coupled with beta-alanine benzyl ester (VIII) to give amide (IX).After hydrogenolysis of the benzyl ester of (IX),the acetate esters were removed by treatment with ammonia in MeOH,THF.
📌 参考资料/链接：
参考文献标题:Synthesis of Tn,sialyl Tn and HIV-1-derived peptide antigen conjugates having a lipid A analog as an immunoadjuvant for synthetic vaccines
文献作者:Miyajima,K.; Nekado,T.; Ikeda,K.; Achiwa,K.
参考来源:Chem Pharm Bull 1998,46(11),1676
📄 详细内容
合成路线:Phenylsulfanyl glycoside (I) was coupled with serine derivative (II) in the presence of N-bromosuccinimide,iodine and tetrabutylammonium triflate yielding the serine glycoside (III).Reductive cleavage of the trichloroethoxy carbonyl group of (III) with Zn and HOAc afforded amine (IV),which was acylated with (R)-3-(tetradecanoyloxy)tetradecanoic acid (V) using DCC and HOBt.Hydrogenolysis of the benzyl ester (VI) over palladium black provided carboxylic acid (VII).
合成路线:Intermediate (VII) was coupled with beta-alanine benzyl ester (VIII) to give amide (IX).After hydrogenolysis of the benzyl ester of (IX),the acetate esters were removed by treatment with ammonia in MeOH,THF.
参考文献标题:Lipid A and related compounds.XXXVII.Determination of favorable binding linkages of lipid A analog to antigen moiety for synthetic vaccines
文献作者:Ikeda,K.; Miyajima,K.; Shimizu,T.; Achiwa,K.
参考来源:Chem Pharm Bull 2000,48(1),32
合成路线:Intermediate (VII) was coupled with beta-alanine benzyl ester (VIII) to give amide (IX).After hydrogenolysis of the benzyl ester of (IX),the acetate esters were removed by treatment with ammonia in MeOH,THF.
参考文献标题:Synthesis of TN and sialyl TN antigen-lipid an analog conjugates for synthetic vaccines
文献作者:Miyajima,K.; Nekado,T.; Ikeda,K.; Achiwa,K.
参考来源:Chem Pharm Bull 1997,45(9),1544