(2S,3S,4R)-3,4-O-isopropylidene-5-phenyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-pentanetriol | 956104-47-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3S,4R)-3,4-O-isopropylidene-5-phenyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-pentanetriol
• CAS: 956104-47-5
• 化学式: C₇₂H₁₀₁NO₉
• 分子量: 1124.6
• InChiKey: MQLNHHKWECWSNM-SNKSLQNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.55
• 重原子数：
  82.0
• 可旋转键数：
  42.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-3,4-O-isopropylidene-5-phenyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-pentanetriol 在 盐酸 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 4.5h， 生成 (2S,3S,4R)-1-O-(α-D-galactosyl)-5-phenyl-2-tetracosanoylamino-1,3,4-pentanetriol
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025
• 作为产物：
  描述：

  4,5-anhydro-1,3-O-benzylidene-D-arabinitol 在 吡啶 、 盐酸 、 copper(l) iodide 、 sodium azide 、 三氟化硼乙醚 、 氢气 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 102.0h， 生成 (2S,3S,4R)-3,4-O-isopropylidene-5-phenyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-pentanetriol
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025

文献信息

• Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs
  作者：Tetsuya Toba、Kenji Murata、Kyoko Nakanishi、Bitoku Takahashi、Naohiro Takemoto、Minako Akabane、Takashi Nakatsuka、Seiichi Imajo、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.bmcl.2007.02.081

  日期：2007.5

  Analogs of immunomodulatory glycolipid OCH (2) were prepared and minimum structure requirement to exhibit equivalent profiles was disclosed. Analogs bearing non-linear hydrocarbon chain in the phytosphingosine moiety (18, 19) were shown for the first time to possess comparable cytokine inducing profile to 2. Molecular modeling of 2/hCD1d complex based on the crystal structure of alpha-GalCer (1)/hCDld complex is also described. (c) 2007 Elsevier Ltd. All rights reserved.