AC98-6446

Chemical Name: (3S,6R,9S,12R,15S)-12-[4-[4-[4,6-O-(2-Adamantylidene)-alpha-D-mannopyranosyloxy]-alpha-D-mannopyranosyloxy]benzyl]-15-cyclohexylmethyl-9-[1(S)-hydroxy-1-[2-iminoimidazolidin-4(S)-yl]methyl]-6-[1(R)-hydroxy-1-[2-imino-3-(alpha-D-mannopyranosyl)imidazolidin-4(S)-yl]methyl]-3-(hydroxymethyl)-1,4,7,10,13,16-hexaazacyclooctadecane-2,5,8,11,14,17-hexaone; Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-(4,6-O-tricyclo[3.3.1.13,7]decylidene-alpha-D-manno-hexopyranosyl)-alpha-D-manno-hexopyranosyl]-D-tyrosyl-3(S)-[2-amino-4,5-dihydro-1H-imidazol-4(S)-yl]-L-seryl-3(R)-[2-amino-1-(alpha-D-manno-hexopyranosyl)-4,5-dihydro-1H-imidazol-5(S)-yl]-D-seryl-L-serylglycyl]
CAS No. 474232-56-9 (undefined stereochem.)
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The title compound is obtained by ketalization of glycopeptide AC98-0053 (I) with adamantanone dimethyl ketal (II) under acidic conditions in DMSO.In turn,glycopeptide (I) can be obtained by two different ways:1) Through biosynthetic precursor feeding of cyclohexylalanine to fermentation broths of certain strains of S.hygroscopicus (this method permits only small quantities of (I)).2) By selective hydrogenation of glycopeptide AC98-7809 (III) 杘btained from high-yielding mutants of S.hygroscopicus- employing Rh/C in aqueous AcOH.(By following this general process it is possible to scale-up the whole process to prepare several hundred grams of the title product).