SS-555
Chemical Name: 6,6'-Di-O-octanoyl-alpha,alpha-trehalose; 6-O-Octanoyl-alpha-D-glucopyranosyl alpha-D-glucopyranoside 6-octanoate
CAS No. 84396-33-8
项目整合开发状态: Preclinical
项目研究机构: Japan Tobacco (Originator), SSP (Originator)
合成路线:2,2',3,3'-Tetra-O-benzyl-alpha,alpha-trehalose (III) was prepared by condensation of trehalose (I) with benzaldehyde,followed by alkylation of the resulting bisbenzylidene derivative (II) with benzyl chloride and then acid hydrolysis of the benzylidene ketal.Acylation of (III) with octanoyl chloride (IV) in the presence of pyridine provided diester (V).Finally,catalytic hydrogenolysis of the benzyl protecting groups yielded the title compound.
📌 参考资料/链接：
参考文献标题:Antitumor formulation containing lipopolysaccharide with trehalose derivs.
文献作者:Fukushi,K.(SSP Co.,Ltd.)
参考来源:US 4612304
📄 详细内容
合成路线:2,2',3,3'-Tetra-O-benzyl-alpha,alpha-trehalose (III) was prepared by condensation of trehalose (I) with benzaldehyde,followed by alkylation of the resulting bisbenzylidene derivative (II) with benzyl chloride and then acid hydrolysis of the benzylidene ketal.Acylation of (III) with octanoyl chloride (IV) in the presence of pyridine provided diester (V).Finally,catalytic hydrogenolysis of the benzyl protecting groups yielded the title compound.
参考文献标题:alphaalpha-Trehalose-6,6'-middle chained aliphatic acid diester and a pharmaceutical agent containing the same
文献作者:Kukita,K.; Shibata,A.; Katori,T.; Nishikawa,Y.; Yoshimoto,K.(SSP Co.,Ltd.)
参考来源:DE 3241199; FR 2534259; GB 2133399