MBX-300, NMSO3
Chemical Name: 5-Acetamido-2-O-[2,2-bis(docosyloxymethyl)propyl]-3,5-dideoxy-4,7,8,9-tetra-O-sulfo-D-glycero-D-galacto-2-nonulopyranosuronic acid pentasodium salt; N-Acetyl-2-O-[3-(docosyloxy)-2-(docosyloxymethyl)-2-methylpropyl]-alpha-neuraminic acid 4,7,8,9-tetrakis(hydrogen sulfate) pentasodium salt
CAS No. 199601-01-9
项目整合开发状态: Preclinical
项目研究机构: Nissin Food Products (Originator), Microbiotix (Licensee)
合成路线:Treatment of 1,1,1-tris(hydroxymethyl)ethane (I) in DMF with NaH and docosyl bromide (II) in benzene yields 2,2,-bis(docosyloxymethyl) propanol (III),which is then condensed with pentaacetyl-2-chloro-2-deoxyneuraminic acid methyl ester (IV) (1) by means of Hg(CN)2 and HgBr2 in CHCl3 to provide the pentaacetylated compound (V).Hydrolysis of (V) by treatment with NaOMe and NaOH in THF:MeOH affords derivative (VI),which is finally converted into the target compound by reaction with sulfur trioxide-trimethylamine complex (SO3.(CH3)3N) in DMF followed by treatment with Dowex 50W-X8 (Na form) resin.
📌 参考资料/链接：
参考文献标题:Novel cpds.having antiviral activity
文献作者:Numata,M.; Nunomura,S.; Terada,M.; Suzuki,K.; Sugimoto,M.; Fujita,S.(Nissin Food Products Co.,Ltd.)
参考来源:CA 2255070; EP 0957107; WO 9743296
📄 详细内容
合成路线:Treatment of 1,1,1-tris(hydroxymethyl)ethane (I) in DMF with NaH and docosyl bromide (II) in benzene yields 2,2,-bis(docosyloxymethyl) propanol (III),which is then condensed with pentaacetyl-2-chloro-2-deoxyneuraminic acid methyl ester (IV) (1) by means of Hg(CN)2 and HgBr2 in CHCl3 to provide the pentaacetylated compound (V).Hydrolysis of (V) by treatment with NaOMe and NaOH in THF:MeOH affords derivative (VI),which is finally converted into the target compound by reaction with sulfur trioxide-trimethylamine complex (SO3.(CH3)3N) in DMF followed by treatment with Dowex 50W-X8 (Na form) resin.
参考文献标题:
文献作者:
参考来源:Chem Ber I 1966,99611