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【结 构 式】

【分子编号】53160

【品名】methyl 3-[({[(2S,3R,4R,5R,6R)-3-(acetylamino)-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}methyl)(ethoxy)phosphoryl]-2-methylpropanoate

【CA登记号】n/a

【 分 子 式 】C16H30NO10P

【 分 子 量 】427.388702

【元素组成】C 44.97% H 7.08% N 3.28% O 37.44% P 7.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

Mesylate (II), prepared from the (hydroxymethyl)phosphinic acid derivative (I), was condensed with the protected glucosamine (III) in the presence of NaH to produce the phosphinate adduct (IV) as a diastereomeric mixture. Selective removal of the P-acetyl ketal group of (IV) with chlorotrimethylsilane and a trace of water gave rise to the deprotected phosphinate (V). This was subjected to Arbuzov reaction with methyl (bromomethyl)acrylate (VI) under silylating conditions to afford the substituted phosphinate (VII). Concomitant double-bond hydrogenation and hydrogenolysis of the benzyl and benzylidene groups of (VII) was effected by hydrogenation over Pd/C. The resulting product (VIII) was then peracetylated with acetic anhydride/pyridine to give the triacetate (IX). Treatment of (IX) with aminoethanol in THF selectively removed the anomeric acetate to produce (X) as a complex diastereomeric mixture.

1 Reck, F.; et al.; Inhibitors of the bacterial cell wall biosynthesis enzyme MurC. Bioorg Med Chem Lett 2001, 11, 11, 1451.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 53154 ethyl 1,1-diethoxyethyl(hydroxymethyl)phosphinate n/a C9H21O5P 详情 详情
(II) 53155 [(1,1-diethoxyethyl)(ethoxy)phosphoryl]methyl methanesulfonate n/a C10H23O7PS 详情 详情
(III) 53156 N-[(2R,4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide n/a C22H25NO6 详情 详情
(IV) 53157 ethyl {[(2R,4aR,6S,7R,8R,8aR)-7-(acetylamino)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}methyl(1,1-diethoxyethyl)phosphinate n/a C31H44NO10P 详情 详情
(V) 53158 ethyl {[(2R,4aR,6S,7R,8R,8aR)-7-(acetylamino)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}methylphosphinate n/a C25H32NO8P 详情 详情
(VI) 32407 methyl 2-(bromomethyl)acrylate C5H7BrO2 详情 详情
(VII) 53159 methyl 2-{[({[(2R,4aR,6S,7R,8R,8aR)-7-(acetylamino)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}methyl)(ethoxy)phosphoryl]methyl}acrylate n/a C30H38NO10P 详情 详情
(VIII) 53160 methyl 3-[({[(2S,3R,4R,5R,6R)-3-(acetylamino)-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}methyl)(ethoxy)phosphoryl]-2-methylpropanoate n/a C16H30NO10P 详情 详情
(IX) 53161 methyl 3-[[({(2R,3R,4R,5R,6R)-3-(acetylamino)-2,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-4-yl}oxy)methyl](ethoxy)phosphoryl]-2-methylpropanoate n/a C22H36NO13P 详情 详情
(X) 53162 methyl 3-[[({(3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-hydroxytetrahydro-2H-pyran-4-yl}oxy)methyl](ethoxy)phosphoryl]-2-methylpropanoate n/a C20H34NO12P 详情 详情
Extended Information