2-[bis(allyloxy)phosphoryloxy]ethyl 3-O-decyl-6-O-{2-deoxy-4-O-[bis(allyloxy)phosphoryl]-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-2-O-(3-oxotetradecanoyl)-α-D-glucopyranoside | 721456-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[bis(allyloxy)phosphoryloxy]ethyl 3-O-decyl-6-O-{2-deoxy-4-O-[bis(allyloxy)phosphoryl]-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-2-O-(3-oxotetradecanoyl)-α-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-2-[2-bis(prop-2-enoxy)phosphoryloxyethoxy]-6-[[(2R,3R,4R,5S,6R)-5-bis(prop-2-enoxy)phosphoryloxy-4-[(3R)-3-methoxydecoxy]-6-(methoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxymethyl]-4-decoxy-5-hydroxyoxan-3-yl] 3-oxotetradecanoate
• CAS: 721456-66-2
• 化学式: C₆₅H₁₁₄Cl₃NO₂₂P₂
• 分子量: 1429.92
• InChiKey: UORVOADYNRMUKF-UTNNSDQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  93
• 可旋转键数：
  62
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  265
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  2-[bis(allyloxy)phosphoryloxy]ethyl 3-O-decyl-6-O-{2-deoxy-4-O-[bis(allyloxy)phosphoryl]-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-2-O-(3-oxotetradecanoyl)-α-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of lipid A analogues containing glucose instead of glucosamine and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing glucose in substitution for glucosamine on the reducing end were synthesized, and the inhibitory activities on LPS-induced TNF alpha production (LPS-antagonistic activity) in vitro using human whole blood cells were measured. The IC50 values (nM) of these ten compounds, 8, 14, 21, 31, 40, 51, 57, 62, 67 and 72, were 11.2, 15.4, 2.7, 0.1, 0.4, 1.3, 3.2, 3.2, 1.4 and 14.4, respectively. And also inhibitory activities (ID50) on TNF alpha production toward galactosamine loaded C3H/HeN mice in vivo of compounds 21, 31, 57, 62 and 67 were measured. The values of these compounds were 0.29, 0.50, 0.61, not dose-dependent and 0.33 mg/kg, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.034
• 作为产物：
  描述：

  Acetic acid (4aR,6S,7R,8S,8aR)-8-decyloxy-2,2-dimethyl-6-(2-oxo-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 四氮唑 、 氢氧化钾 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 双氧水 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 sodium sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 23.92h， 生成 2-[bis(allyloxy)phosphoryloxy]ethyl 3-O-decyl-6-O-{2-deoxy-4-O-[bis(allyloxy)phosphoryl]-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-2-O-(3-oxotetradecanoyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of lipid A analogues containing glucose instead of glucosamine and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing glucose in substitution for glucosamine on the reducing end were synthesized, and the inhibitory activities on LPS-induced TNF alpha production (LPS-antagonistic activity) in vitro using human whole blood cells were measured. The IC50 values (nM) of these ten compounds, 8, 14, 21, 31, 40, 51, 57, 62, 67 and 72, were 11.2, 15.4, 2.7, 0.1, 0.4, 1.3, 3.2, 3.2, 1.4 and 14.4, respectively. And also inhibitory activities (ID50) on TNF alpha production toward galactosamine loaded C3H/HeN mice in vivo of compounds 21, 31, 57, 62 and 67 were measured. The values of these compounds were 0.29, 0.50, 0.61, not dose-dependent and 0.33 mg/kg, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.034