|
【结 构 式】 
|
【分子编号】57552 【品名】(1R)-1-{2-[((2R,3S,4R,5R)-3-[(diphenoxyphosphoryl)oxy]-2-(methoxymethyl)-6-[(2,2,2-trichloroethanimidoyl)oxy]-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-4-yl)oxy]ethyl}dodecyl myristate 【CA登记号】 |
【 分 子 式 】C52H79Cl6N2O12P 【 分 子 量 】1167.895502 【元素组成】C 53.48% H 6.82% Cl 18.21% N 2.4% O 16.44% P 2.65% |
合成路线1
该中间体在本合成路线中的序号：(XXIX)The glucosamine derivative (XXVIII) is activated as the imidate (XXIX), upon treatment with trichloroacetonitrile and DBU, and subsequently coupled with (XI) in the presence of trimethylsilyl triflate, to afford disaccharide (XXX). The trichloroethoxycarbonyl protecting group of (XXX) is then removed by reductive treatment with zinc and acetic acid, producing amine (XXXI), which is subsequently acetylated with Ac2O, to afford acetamide (XXXII).
| 【1】 Nishijima, M.; Kurakata, S.-I.; Shiozaki, M.; Mochizuki, T.; Kanai, S.; Watanabe, Y.; Synthesis of lipid A type pyran carboxylic acids with ether chains and their biological activities. Carbohydr Res 2001, 333, 3, 203. |
| 【2】 Shiozaki, M.; Kurakata, S.; Kanai, S.; Kazama, Y. (Sankyo Co., Ltd.); Ether type lipid A1-carboxylic acid analogues. EP 1152007; JP 2000297096; US 2002161221; US 6511965; WO 0047595 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 57535 | benzhydryl (2S,3R,4R,5S,6R)-3-{[(3R)-3-(benzyloxy)tetradecanoyl]amino}-4-{[(3R)-3-(benzyloxy)tetradecyl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate | C62H89NO9 | 详情 | 详情 | |
| (XXVIII) | 57551 | (1R)-1-{2-[((2R,3S,4R,5R)-3-[(diphenoxyphosphoryl)oxy]-6-hydroxy-2-(methoxymethyl)-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-4-yl)oxy]ethyl}dodecyl myristate | C50H79Cl3NO12P | 详情 | 详情 | |
| (XXIX) | 57552 | (1R)-1-{2-[((2R,3S,4R,5R)-3-[(diphenoxyphosphoryl)oxy]-2-(methoxymethyl)-6-[(2,2,2-trichloroethanimidoyl)oxy]-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-4-yl)oxy]ethyl}dodecyl myristate | C52H79Cl6N2O12P | 详情 | 详情 | |
| (XXX) | 57553 | benzhydryl (2S,3R,4R,5S,6R)-3-{[(3R)-3-(benzyloxy)tetradecanoyl]amino}-4-{[(3R)-3-(benzyloxy)tetradecyl]oxy}-6-{[((2R,3R,4R,5S,6R)-5-[(diphenoxyphosphoryl)oxy]-6-(methoxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecyl]oxy}-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl)oxy]methyl}-5-hydroxytetrahydro-2H-pyran-2-carboxylate | C112H166Cl3N2O20P | 详情 | 详情 | |
| (XXXI) | 57554 | benzhydryl (2S,3R,4R,5S,6R)-6-{[((2R,3R,4R,5S,6R)-3-amino-5-[(diphenoxyphosphoryl)oxy]-6-(methoxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecyl]oxy}tetrahydro-2H-pyran-2-yl)oxy]methyl}-3-{[(3R)-3-(benzyloxy)tetradecanoyl]amino}-4-{[(3R)-3-(benzyloxy)tetradecyl]oxy}-5-hydroxytetrahydro-2H-pyran-2-carboxylate | C109H165N2O18P | 详情 | 详情 | |
| (XXXII) | 57555 | benzhydryl (2S,3R,4R,5S,6R)-6-{[((2R,3R,4R,5S,6R)-3-(acetylamino)-5-[(diphenoxyphosphoryl)oxy]-6-(methoxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecyl]oxy}tetrahydro-2H-pyran-2-yl)oxy]methyl}-3-{[(3R)-3-(benzyloxy)tetradecanoyl]amino}-4-{[(3R)-3-(benzyloxy)tetradecyl]oxy}-5-hydroxytetrahydro-2H-pyran-2-carboxylate | C111H167N2O19P | 详情 | 详情 |