|
【结 构 式】 
|
【分子编号】64191 【品名】allyl (2R,3S,4R,5R)-2-({[(2R,3R,4R,5S,6R)-3-amino-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate 【CA登记号】 |
【 分 子 式 】C64H119N2O17PSi 【 分 子 量 】1247.711402 【元素组成】C 61.61% H 9.61% N 2.25% O 21.8% P 2.48% Si 2.25% |
合成路线1
该中间体在本合成路线中的序号：(LX)Reduction of the azido group of disaccharide (LVII), followed by acylation of the resultant amine (LVIII) with keto acid (XXXI) produced keto amide (LIX). The Troc protecting group of (LIX) was then removed by reductive treatment with zinc-copper couple in AcOH yielding amine (LX).
| 【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 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXI) | 59107 | 3-oxotetradecanoic acid | C14H26O3 | 详情 | 详情 | |
| (LVII) | 64188 | allyl (2R,3S,4R,5R)-5-azido-2-{[((2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl)oxy]methyl}-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate | C53H94Cl3N4O17PSi | 详情 | 详情 | |
| (LVIII) | 64189 | allyl (2R,3S,4R,5R)-5-amino-2-{[((2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl)oxy]methyl}-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate | C53H96Cl3N2O17PSi | 详情 | 详情 | |
| (LIX) | 64190 | allyl (2R,3S,4R,5R)-2-{[((2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl)oxy]methyl}-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate | C67H120Cl3N2O19PSi | 详情 | 详情 | |
| (LX) | 64191 | allyl (2R,3S,4R,5R)-2-({[(2R,3R,4R,5S,6R)-3-amino-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate | C64H119N2O17PSi | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(LX)Amine (LX) was acylated with cis-vaccenic acid (LXI) to produce amide (LXII). This was desilylated by means of HF yielding alcohol (XXXIX), which was finally converted to the title compound using the same sequence as in Scheme 27814501f.
| 【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 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (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 | |
| (LX) | 64191 | allyl (2R,3S,4R,5R)-2-({[(2R,3R,4R,5S,6R)-3-amino-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate | C64H119N2O17PSi | 详情 | 详情 | |
| (LXI) | 64192 | (Z)-11-octadecenoic acid | C18H34O2 | 详情 | 详情 | |
| (LXIII) | 64193 | 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]-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate | C82H151N2O18PSi | 详情 | 详情 |