allyl (2R,3S,4R,5R,6R)-6-{[bis(allyloxy)phosphoryl]oxy}-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate -Drug Synthesis Database

【结构式】

【分子编号】64172

【品名】allyl (2R,3S,4R,5R,6R)-6-{[bis(allyloxy)phosphoryl]oxy}-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate

【CA登记号】

【分子式】C₈₂H₁₄₆N₂O₂₁P₂

【分子量】1558.009644

【元素组成】C 63.22% H 9.45% N 1.8% O 21.57% P 3.98%

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：(XL)

Hydrolysis of the enol ether group of (XXXVIII) with HF yielded (XXXIX), which was converted to phosphate (XL) by sequential phosphitylation with diallyl N,N-diisopropylphosphoramidite, followed by oxidation with m-chloroperbenzoic acid. The title disaccharide was finally obtained by palladium-catalyzed deprotection of the allyl phosphate and carbonate ester groups of (XL).

参考文献中间体

合成目标

【1】 Kobayashi, S.; Kawata, T.; Christ, W.J.; Rossignol, D.P. (Eisai Co., Ltd.); Substd. liposaccharides useful in the treatment and prevention of endotoxemia. US 5750664; WO 9639411 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXXVIII)	64170	allyl (2R,3S,4R,5R)-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]-6-[(Z)-1-propenyloxy]tetrahydro-2H-pyran-3-yl carbonate	C₇₉H₁₄₁N₂O₁₈P	详情	详情
(XXXIX)	64171	allyl (2R,3S,4R,5R)-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-4-(decyloxy)-6-hydroxy-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate	C₇₆H₁₃₇N₂O₁₈P	详情	详情
(XL)	64172	allyl (2R,3S,4R,5R,6R)-6-{[bis(allyloxy)phosphoryl]oxy}-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate	C₈₂H₁₄₆N₂O₂₁P₂	详情	详情

Extended Information