新产品编号:2446281

Chemical Name: trans,trans-4'-[4-[1-O-Butyl-2-[3(R)-[butyl(hydroxy)phosphoryloxy]octanamido]-3-O-[3(R)-[butyl(hydroxy)phosphoryloxy]octanoyl]-4-O-(phosphono)-2-deoxy-beta-D-glucopyranos-6-O-ylcarbonyl]-1,1'-bi(cyclohexyl)-4-carboxylic acid; trans,trans-1-O-Butyl-2-[
项目整合开发状态: Preclinical
项目研究机构: Scripps Research Institute (Originator)
合成路线:Transesterification of the butyl glycoside triacetate (I) with NaOMe/MeOH provides triol (II).The 4- and 6-hydroxyl groups of (II) are then protected by formation of the benzylidene acetal (III) with alpha,alpha-dimethoxytoluene in the presence of p-toluenesulfonic acid.Removal of the N-acetyl group of (III) with hydrazine in EtOH furnishes the amino alcohol intermediate (IV).

合成路线:Condensation of the chiral beta-hydroxy ester (V) with butylphosphonic dichloride (VI) in the presence of tetrazole,followed by addition of benzyl alcohol to the intermediate mono-chloride (VII) leads to phosphonate (VIII).The t-butyl ester group of (VIII) is then removed by treatment with trifluoroacetic acid,producing carboxylic acid (IX).This is subsequently coupled to the amino alcohol (IV) to furnish the N,O-diacylated glycoside (X).Further acidic ketal hydrolysis in (X) gives rise to diol (XI).

合成路线:The primary hydroxyl group of diol (XI) is esterified with the dicyclohexyl carboxylic acid (XII) providing ester (XIII).The remaining secondary hydroxyl of (XIII) is then acylated with the cyclic phosphoramidite (XIV),followed by oxidation with m-chloroperbenzoic acid to afford phosphate (XV).Finally,catalytic hydrogenolysis of the benzyl ester groups of (XV) leads to the title compound.