新产品编号:956037
Chemical Name: (3S,6R,9S,12R,15S)-9-[1(S)-Hydroxy-1-[2-iminoimidazolidin-4(S)-yl]methyl]-6-[1(S)-hydroxy-1-[2-imino-3-(alpha-D-mannopyranosyl)imidazolidin-4(S)-yl]methyl]-3-(hydroxymethyl)-12-[4-[4-O-(6-methoxynaphthalen-2-ylmethyl)-alpha-D-mannopyranosyl-(1-4)-alpha-D-mannopyranosyloxy]benzyl]-15-[1(S)-phenylethyl]-1,4,7,10,13,16-hexaazacyclooctadecane-2,5,8,11,14,17-hexaone
CAS No. 474233-81-3 (undefined stereoch.)
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:Reaction of mannopeptimycin-alpha (I) with 6-methoxy-2-naphthaldehyde dimethyl acetal (II) under acidic conditions leads to a mixture of regioisomeric naphthylmethylidene acetals (III) and (IV) on the terminal mannose moiety (1-3).
合成路线:Reductive ring opening of the mixture of acetals (III) and (IV) by means of NaBH3CN and trifluoroacetic acid produces the corresponding mixture of 2-,3-,4- and 6-O-naphthylmethyl ethers,from which the target 4-O-ether is isolated by preparative HPLC (1-3).
📌 参考资料/链接：
参考文献标题:Glycopeptide antibiotics
文献作者:Sum,P.-E.; Newman,H.; Greenstein,M.; Sakya,S.; He,H.; Dushin,R.G.; Lang,S.A.; Abbanat,D.R.; Bernan,V.S.; Sutherland,A.G.; Wang,T.-Z.; Ruppen,M.E.; Bailey,A.E.; Chi,P.; Shen,B.; Kong,F.; Lotvin,J.A.(Wyeth)
参考来源:WO 0285307
📄 详细内容
合成路线:Reaction of mannopeptimycin-alpha (I) with 6-methoxy-2-naphthaldehyde dimethyl acetal (II) under acidic conditions leads to a mixture of regioisomeric naphthylmethylidene acetals (III) and (IV) on the terminal mannose moiety (1-3).
合成路线:Reductive ring opening of the mixture of acetals (III) and (IV) by means of NaBH3CN and trifluoroacetic acid produces the corresponding mixture of 2-,3-,4- and 6-O-naphthylmethyl ethers,from which the target 4-O-ether is isolated by preparative HPLC (1-3).
参考文献标题:Glycopeptide antibiotic
文献作者:Greenstein,M.; He,H.; Abbanat,D.R.; Bernan,V.S.; Sutherland,A.G.; Ruppen,M.E.; Bailey,A.E.; Lotvin,J.A.(Wyeth)
参考来源:WO 0286141
合成路线:Reaction of mannopeptimycin-alpha (I) with 6-methoxy-2-naphthaldehyde dimethyl acetal (II) under acidic conditions leads to a mixture of regioisomeric naphthylmethylidene acetals (III) and (IV) on the terminal mannose moiety (1-3).
合成路线:Reductive ring opening of the mixture of acetals (III) and (IV) by means of NaBH3CN and trifluoroacetic acid produces the corresponding mixture of 2-,3-,4- and 6-O-naphthylmethyl ethers,from which the target 4-O-ether is isolated by preparative HPLC (1-3).
参考文献标题:Novel ether derivatives of mannopeptimycin glycopeptide antibiotic
文献作者:Sum,P.-E.; How,D.; Torres,N.; Petersen,P.J.; Lenoy,E.B.; Weiss,W.J.; Mansour,T.S.
参考来源:Bioorg Med Chem Lett 2003,13(6),1151