(R)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-1-ol | 862718-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-1-ol
• CAS: 862718-90-9
• 化学式: C₄₇H₆₀O₈
• 分子量: 752.989
• InChiKey: RPDBMDSWHBBFGE-PCJBZQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  55.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-1-ol 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Tetracosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-octyl}-amide
  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：

  (4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde 在 正丁基锂 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 10.0h， 生成 (R)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-1-ol
  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

• A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH
  作者：Tetsuya Toba、Kenji Murata、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.tetlet.2005.05.069

  日期：2005.7

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.