Dalbavancin, V-Glycopeptide, VER-001, BI-397 factor B0, BI-397

达巴万星Chemical Name: 5,31-Dichloro-38-de(methoxycarbonyl)-7-demethyl-19-deoxy-56-O-[2-deoxy-2-(10-methylundecanamido)-beta-D-glucopyranuronosyl]-38-[N-[3-(dimethylamino)propyl]carbamoyl]-42-O-alpha-D-mannopyranosyl-N15-methylristomycin A aglycone; (3S,15R,18R,34R,35S,48S,50aR)-5,31-Dichloro-56-[2-deoxy-2-(10-methyl-1-oxoundecylamino)-6-carboxy]-beta-D-glucopyranosyloxy]-N-[3-(dimethylamino)propyl]-6,11,34,40,44-pentahydroxy-42-(alpha-D-mannopyranosyloxy)-15-(methylamino)-2,16,36,50,51,59-hexaoxo-2,3,16,17,18,19,35,36,37,38,48,49,50,50a-tetradecahydro-1H,15H,34H-20,23:30,33-dietheno-3,18:35,48-bis(iminomethano)-4,8:10,14:25,28:43,47-tetrametheno[1,14,6,22]dioxadiazacyclooctacosino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-38-carboxamide
CAS No. 171500-79-1
项目整合开发状态: Phase III
项目研究机构: Vicuron Pharmaceuticals (Originator), Vicuron Pharmaceuticals (Licensee)
合成路线:BI 397 is the 3-(dimethylamino)-1-propylamide at the peptide-carboxy group of the natural glycopeptide A-40,926.BI 397 is prepared from A-40,926 following a three-step procedure which consists of: 1) selective methyl esterification of the N-acylaminoglucuronic acid function,2) amidation of the peptide-carboxy group and 3) saponification of the sugar methyl ester.Steps 2 and 3 are performed in one-pot.Step 1): Reaction of A-40,926 (A) (I) in methanol in the presence of H2SO4 at 0-5 C for 24 h gives the monomethyl ester (MA) (II) at the sugar-carboxy group (80% yield).Step 2): Amidation at the peptide-carboxy group is carried out by reaction of MA (II) with 3-(dimethylamino)-1-propylamine (DMEPA) (III) in DMSO in the presence of PyBOP to obtain the methyl ester (MA-A-1) (IV) of BI 397; this compound is not isolated.Step 3): Hydrolysis of MA-A-1 (IV) in the above DMSO solution with 15% NAOH gives BI 397 (A-A-1,63% yield from MA).