【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% |
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 |