(2R,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl 2,2,2-trichloroethyl carbonate -Drug Synthesis Database

【结构式】

【分子编号】40619

【品名】(2R,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl 2,2,2-trichloroethyl carbonate

【CA登记号】

【分子式】C₁₉H₂₁Cl₆NO₉

【分子量】620.09328

【元素组成】C 36.8% H 3.41% Cl 34.3% N 2.26% O 23.22%

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：(XV)

In a related procedure for the synthesis of the protected precursor (XIV), the known bis(trichloroethoxycarbonyl) derivative (XV) was coupled with glycosyl chloride (XII) to give the corresponding disaccharide which was deprotected to (XVI) upon treatment with Zn/AcOH. Bis N-acylation of (XV) with acid (II) in the presence of EEDQ then provided the target intermediate (XIV).

参考文献中间体

合成目标

【1】 Sowell, C.G.; Johnson, D.A.; Keegan, D.S.; et al.; 3-O-Desacyl monophosphoryl lipid A derivatives: Synthesis and immunostimulant activities. J Med Chem 1999, 42, 22, 4640.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(II)	40612	(3R)-3-(tetradecanoyloxy)tetradecanoic acid	C₂₈H₅₄O₄	详情	详情
(XII)	40616	(2R,3R,4R,5S,6R)-2-chloro-5-[(diphenoxyphosphoryl)oxy]-6-([[(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl]oxy]methyl)-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate	C₅₄H₇₉Cl₇NO₁₄P	详情	详情
(XIV)	40618		C₁₁₅H₁₉₅N₂O₂₁P	详情	详情
(XV)	40619	(2R,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-3-[[(2,2,2-trichloroethoxy)carbonyl]amino]tetrahydro-2H-pyran-4-yl 2,2,2-trichloroethyl carbonate	C₁₉H₂₁Cl₆NO₉	详情	详情
(XVI)	40620	(2R,3R,4R,5R,6R)-3-amino-2-[[(2R,3S,4R,5R,6R)-5-amino-6-(benzyloxy)-3,4-dihydroxytetrahydro-2H-pyran-2-yl]methoxy]-5-[(diphenoxyphosphoryl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate	C₅₉H₉₁N₂O₁₅P	详情	详情

Extended Information