新产品编号:630145

Chemical Name: 2-[[3-[N'-[4-Chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-2-O-[2-deoxy-2-[3-(trifluoromethyl)benzamido]-beta-D-glucopyranosyl]-4-O-methyl-alpha-D-glucopyranos-1-yloxyuronamide](hydroxy)phosphoryloxy]hexadecanoic acid
CAS No. 244292-42-0
项目整合开发状态: Biological Testing
项目研究机构: Aeolus Pharmaceuticals (Originator)
合成路线:The compound was obtained by solid-phase synthesis on an aminoethyl-photolinker AM resin.Deprotection of hydroxyl and amino groups from disaccharide-resin (I) by means of hydrazine provided (II).Reaction of the resulting free C-2' amino group of (II) with 3-(trifluoromethyl)benzoic acid (III) in the presence of HATU afforded the corresponding amide (IV).Reacetylation of (IV) with acetic anhydride and dimethylaminopyridine gave triacetate (V).Subsequent reduction of the azido group of (V) by means of trimethyl phosphine provided the C-3 amine (VI),which was condensed with 4-chloro-3-(trifluoromethyl)phenyl isocyanate (VII) yielding urea (VIII).

合成路线:Cleavage of the anomeric thiophenyl group of (VIII) by means of mercuric trifluoroacetate produced the desired lactol (IX).Attachment of the phospholipid unit to lactol (IX) was carried out by reaction with phosphoramidite (X).The resulting phosphite ester (XI) was then oxidized to phosphate (XII) using meta-chloroperbenzoic acid.Subsequent basic hydrolysis of (XII) removed the protecting groups to give (XIII).Finally,photolytic cleavage of the resin (XIII) furnished the title disaccharide derivative.