allyl 3-O-decyl-2-deoxy-4,6-O-isopropylidene-2-(trifluoroacetyl)amino-α-D-glucopyranoside | 185955-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 3-O-decyl-2-deoxy-4,6-O-isopropylidene-2-(trifluoroacetyl)amino-α-D-glucopyranoside
• 英文别名: allyl 3-O-decyl-2-O-deoxy-4,6-O-isopropylidene-2-trifluoroacetylamino-α-D-glucopyranoside；Allyl 3-O-decyl-4-O,6-O-isopropylidene-2-(trifluoroacetylamino)-2-deoxy-alpha-D-glucopyranoside；N-[(4aR,6S,7R,8R,8aS)-8-decoxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trifluoroacetamide
• CAS: 185955-20-8
• 化学式: C₂₄H₄₀F₃NO₆
• 分子量: 495.58
• InChiKey: KDDJBKKDAGNRFA-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 3-O-decyl-2-deoxy-4,6-O-isopropylidene-2-(trifluoroacetyl)amino-α-D-glucopyranoside 在 四氮唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 WSC*HCl 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 19.08h， 生成 2-(dialylphosphonooxy)ethyl 3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing a glucose moiety on their non-reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on LPS-induced TNF alpha production of these six compounds, 26, 33, 440, 520, 59, and 61, toward human whole blood cells were 0.49, 0.65, 0.51, 0.98, 0.46, and 1.11 nM, respectively. Inhibitory doses (ID50) of compounds 26, 33, 440, 59, and 61 on TNF alpha production induced by coinjection of galactosamine and LPS in C3HMeN mice were measured. The ID50 values of these compounds were 0.45, 0.96, < 0.2, 1.08, and < 0.2 mg/kg, respectively. Moreover, C3H/HeN mice preinjected with compounds 26, 33, and 440 were protected from lethality induced by coinjection of galactosamine and LPS. Out of eight mice preinjected with 1 mg/kg of compounds 26, 33, and 440, five, eight and six mice were protected, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.115
• 作为产物：
  描述：

  methanesulfonic acid decyl ester 、 2-丙烯-1-基 2-脱氧-4,6-O-(1-甲基乙亚基)-2-[(2,2,2-三氟乙酰基)氨基]-alpha-D-吡喃葡萄糖苷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到allyl 3-O-decyl-2-deoxy-4,6-O-isopropylidene-2-(trifluoroacetyl)amino-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing a glucose moiety on their non-reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on LPS-induced TNF alpha production of these six compounds, 26, 33, 440, 520, 59, and 61, toward human whole blood cells were 0.49, 0.65, 0.51, 0.98, 0.46, and 1.11 nM, respectively. Inhibitory doses (ID50) of compounds 26, 33, 440, 59, and 61 on TNF alpha production induced by coinjection of galactosamine and LPS in C3HMeN mice were measured. The ID50 values of these compounds were 0.45, 0.96, < 0.2, 1.08, and < 0.2 mg/kg, respectively. Moreover, C3H/HeN mice preinjected with compounds 26, 33, and 440 were protected from lethality induced by coinjection of galactosamine and LPS. Out of eight mice preinjected with 1 mg/kg of compounds 26, 33, and 440, five, eight and six mice were protected, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.115

文献信息

• EP1702926
  申请人：——

  公开号：——

  公开（公告）日：——
• Substituted Liposaccharides Useful in the Treatment and Prevention of Endotoxemia
  申请人：Christ William J.

  公开号：US20080214802A1

  公开（公告）日：2008-09-04

  Novel substituted liposaccharides useful as in the prophylactic and affirmative treatment of endotoxemia including sepsis, septicemia and various forms of septic shock and methods of using these agents are provided. Also provided are methods of preparing these agents and intermediates useful therein.
• REAGENTS AND METHODS FOR PREPARING LPS ANTAGONIST B1287 AND STEREOISOMERS THEREOF
  申请人：Fan RuLin

  公开号：US20110152508A1

  公开（公告）日：2011-06-23

  The present invention provides methods for preparing LPS antagonist lipodisaccharide B1287 and stereoisomers thereof, which compounds are useful as in the prophylactic and affirmative treatment of endotoxemia including sepsis, septicemia and various forms of septic shock. Also provided are synthetic intermediates useful for implementing the inventive methods.
• US7737129B2
  申请人：——

  公开号：US7737129B2

  公开（公告）日：2010-06-15
• US7906633B2
  申请人：——

  公开号：US7906633B2

  公开（公告）日：2011-03-15