OJ-R9188

Chemical Name: N-(2-Tetradecylhexadecanoyl)-O-(alpha-L-fucofuranosyl)-D-seryl-L-glutamic acid methylamide L-arginine
CAS No. 190586-70-0, 190586-39-1 (free base)
项目整合开发状态: Preclinical
项目研究机构: Nippon Organon (Originator)
合成路线:Coupling of N-Boc-D-serine (I) with L-glutamic acid 1-methylamide 5-benzyl ester (II) by means of EDC and HOBt affords the dipeptide derivative (III).Subsequent glycosylation of the serine hydroxyl group of (III) with the perbenzylfucose donor (IV) in the presence of SnCl2 and AgOTf gives the alpha-glycoside (V).The N-Boc protecting group of (V) is removed under acidic conditions to furnish amine (VI),which is acylated by 2-tetradecylhexadecanoic acid (VII),yielding amide (VIII).The O-benzyl protecting groups of (VIII) are then removed by hydrogenolysis in the presence of Pearlman's catalyst,and the resultant carboxylic acid is finally converted to the corresponding arginine salt.