[(4R,5R)-5-(naphthalen-2-ylmethoxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol | 947747-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(4R,5R)-5-(naphthalen-2-ylmethoxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
• CAS: 947747-18-4
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: KPMBHANTEOWCQC-JAZPPYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4R,5R)-5-(naphthalen-2-ylmethoxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol 在 dimethyl sulfide borane 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(2R,3R)-3-(benzyloxy)-4-(naphthalen-2-ylmethoxy)butane-1,2-diol
  参考文献：
  名称：

  Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

  摘要：

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.161
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 [(4R,5R)-5-(naphthalen-2-ylmethoxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

  摘要：

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.161

文献信息

• Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides
  作者：Takashi Tsujimoto、Yukishige Ito

  DOI：10.1016/j.tetlet.2007.05.161

  日期：2007.7

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.