{(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl hydrogen 4-morpholinylphosphonate -Drug Synthesis Database

【结构式】

【分子编号】53165

【品名】{(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl hydrogen 4-morpholinylphosphonate

【CA登记号】n/a

【分子式】C₁₃H₂₀N₃O₉P

【分子量】393.290382

【元素组成】C 39.7% H 5.13% N 10.68% O 36.61% P 7.88%

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：(XIII)

Treatment of (X) with BuLi and diphenyl chlorophosphate led to stereoselective formation of the alpha phosphate ester (XI). The phenyl phosphate ester groups of (XI) were then deprotected by catalytic hydrogenation over PtO2 to afford (XII), isolated as a mixture of two major diastereomers. Coupling of (XII) with uridine monophosphate morpholidate (XIII) led to the uridine diphosphate-containing derivative (XIV). Finally, saponification of the ester groups of (XIV) with aqueous NaOH furnished the title compound.

参考文献中间体

合成目标

【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
(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
(XI)	53163	methyl 3-[[({(2R,3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-[(diphenoxyphosphoryl)oxy]tetrahydro-2H-pyran-4-yl}oxy)methyl](ethoxy)phosphoryl]-2-methylpropanoate	n/a	C₃₂H₄₃NO₁₅P₂	详情	详情
(XII)	53164	methyl 3-[({[(2R,3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-(phosphonooxy)tetrahydro-2H-pyran-4-yl]oxy}methyl)(ethoxy)phosphoryl]-2-methylpropanoate	n/a	C₂₀H₃₅NO₁₅P₂	详情	详情
(XIII)	53165	{(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl hydrogen 4-morpholinylphosphonate	n/a	C₁₃H₂₀N₃O₉P	详情	详情
(XIV)	53166		n/a	C₂₉H₄₆N₃O₂₃P₃	详情	详情

Extended Information