(2R,3S,4R)-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol | 853013-15-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R)-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol
• 英文别名: (2R,3S,4R)-3,4-bis(phenylmethoxy)octadecane-1,2-diol
• CAS: 853013-15-7
• 化学式: C₃₂H₅₀O₄
• 分子量: 498.747
• InChiKey: QAZVCOPSQGRWCI-IWWXRALLSA-N

物化性质

• 沸点：
  625.3±55.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol 在 palladium dihydroxide 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 糖脂
  参考文献：
  名称：

  D-的有效合成核糖-和1- L-来苏-phytosphingosine从d-酒石酸

  摘要：

  D-的制剂核糖-和1- L-来苏-phytosphingosines（1，2）中有所描述。螯合控制的十四烷基溴化镁添加到亚戊基保护的d-苏糖醇醛6中，得到了关键的中间体四萜7，提供了植物鞘氨醇的所需l-lyxo立体化学。中间体7在C4处的转化提供了d-核糖立体化学。

  DOI：

  10.1016/j.tetlet.2005.03.063
• 作为产物：
  描述：

  (2R,3R,4R)-2-O-allyl-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol 在 甲醇 、 palladium dichloride 作用下， 以84%的产率得到(2R,3S,4R)-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol
  参考文献：
  名称：

  Design and synthesis of new KRN7000 analogues

  摘要：

  Presented by CD1d protein, KRN7000, a potent synthetic cc-galactosylceramide, is known to stimulate the iNKT cells to produce different bioactive cytokines. Six new KRN7000 analogues, in which the amide bond in KRN7000 is replaced with O, NH, or ester groups incorporating variation of the acyl chain, or possessing an additional four-atom linker between the galactose and phytosphingosine moiety, were designed and synthesized. The synthetic compounds were evaluated for their ability to stimulate cytokine release and the preliminary structure activity relationships were discussed. The synthetic strategy will benefit the construction of more KRN7000 derivatives, which may contribute to cytokine profile bias. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.051

文献信息

• Design and synthesis of new KRN7000 analogues
  作者：Man Sun、Yuhang Wang、Xin-Shan Ye

  DOI：10.1016/j.tet.2013.06.051

  日期：2013.9

  Presented by CD1d protein, KRN7000, a potent synthetic cc-galactosylceramide, is known to stimulate the iNKT cells to produce different bioactive cytokines. Six new KRN7000 analogues, in which the amide bond in KRN7000 is replaced with O, NH, or ester groups incorporating variation of the acyl chain, or possessing an additional four-atom linker between the galactose and phytosphingosine moiety, were designed and synthesized. The synthetic compounds were evaluated for their ability to stimulate cytokine release and the preliminary structure activity relationships were discussed. The synthetic strategy will benefit the construction of more KRN7000 derivatives, which may contribute to cytokine profile bias. (C) 2013 Elsevier Ltd. All rights reserved.
• An efficient synthesis of d-ribo- and l-lyxo-phytosphingosine from d-tartaric acid
  作者：Xuequan Lu、Robert Bittman

  DOI：10.1016/j.tetlet.2005.03.063

  日期：2005.5

  The preparations of d-ribo- and l-lyxo-phytosphingosines (1, 2) are described. Chelation-controlled addition of tetradecylmagnesium bromide to pentylidene-protected d-threitol aldehyde 6 afforded the key intermediate tetrol 7, providing the desired l-lyxo stereochemistry of phytosphingosine. Inversion at C4 of intermediate 7 provided the d-ribo stereochemistry.

  D-的制剂核糖-和1- L-来苏-phytosphingosines（1，2）中有所描述。螯合控制的十四烷基溴化镁添加到亚戊基保护的d-苏糖醇醛6中，得到了关键的中间体四萜7，提供了植物鞘氨醇的所需l-lyxo立体化学。中间体7在C4处的转化提供了d-核糖立体化学。