allyl 2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 97562-25-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: allyl 2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: allyl 2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside；allyl 2-deoxy-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside；[(2R,3S,4R,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 97562-25-9
• 化学式: C₄₀H₇₀Cl₃NO₁₀
• 分子量: 831.356
• InChiKey: LCTACSKNDBMYLX-GYXRXMPRSA-N

物化性质

• 熔点：
  68-70 °C(Solv: hexane (110-54-3))
• 沸点：
  781.7±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  54
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 allyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives

  摘要：

  The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00326-2
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 盐酸 、 4-二甲氨基吡啶 、 calcium sulfate 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 allyl 2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  脂质A 1-去磷酸衍生物的化学合成

  摘要：

  合成了1-Dephospho大肠杆菌脂质A（），显示与从细菌细胞中分离出的相应衍生物相同。这提供了明确的证据来支持我们最近提出的大肠杆菌脂质A（）的结构。

  DOI：

  10.1016/s0040-4039(00)61962-7

文献信息

• Total Synthesis of<i>Escherichia coli</i>Lipid A, the Endotoxically Active Principle of Cell-Surface Lipopolysaccharide
  作者：Masahiro Imoto、Hiroyuki Yoshimura、Tetsuo Shimamoto、Nobuki Sakaguchi、Shoichi Kusumoto、Tetsuo Shiba

  DOI：10.1246/bcsj.60.2205

  日期：1987.6

  Chemical syntheses are described of polyacylated β(1→6) glucosamine disaccharide 1,4′-bis(phosphate), which corresponds to the proposed structure of E. coli lipid A, and of its dephospho derivatives. The synthetic bisphosphate proved to be identical with the corresponding natural specimen. The chemical structure of lipid A was thus established.

  本文描述了聚酰基化的β(1→6)葡萄糖胺二糖1,4′-二磷酸的化学合成，该化合物对应于拟定的大肠杆菌脂质A的结构，以及其去磷酸衍生物。合成的二磷酸与相应的天然样本相同。因此，脂质A的化学结构得以确立。
• Lipid A-Type Pyrancarboxylic Acid Derivatives, their Synthesis and their Biological Activities
  作者：Takashi Mochizuki、Yuji Iwano、Masao Shiozaki、Shin-ichi Kurakata、Saori Kanai、Masahiro Nishijima

  DOI：10.1016/s0040-4020(00)00684-0

  日期：2000.9

  Synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing sugar part of the disaccharide instead of the phosphoric acid group in lipid A, is described. We investigated the influence of the substituents in the 2'- and 6'-position of the molecules synthesized on their activities toward human monoblastic U937 cells. It was revealed that a series of compounds, possessing an acetamido group in the 2'-position showed strong LPS-antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ——
  作者：SIBA TEHTSUO

  DOI：——

  日期：——
• IMOTO, MASAHIRO;YOSHIMURA, HIROYUKI;SHIMAMOTO, TETSUO;SAKAGUCHI, NOBUKI;K+, BULL. CHEM. SOC. JAP., 60,(1987) N 6, 2205-2214
  作者：IMOTO, MASAHIRO、YOSHIMURA, HIROYUKI、SHIMAMOTO, TETSUO、SAKAGUCHI, NOBUKI、K+

  DOI：——

  日期：——
• US5066794A
  申请人：——

  公开号：US5066794A

  公开（公告）日：1991-11-19