((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)methanol | 325829-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)methanol
• 英文别名: [(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]methanol
• CAS: 325829-94-5
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: BIKHUFBXANBAEP-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)methanol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 palladium on activated charcoal 、 氢气 、 palladium(II) hydroxide 、 碳酸氢钠 、 臭氧 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 1-N-tert-butyloxycarbonyl-3,4-O-isopropylidene-phytosphingosine
  参考文献：
  名称：

  A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine

  摘要：

  The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide 9 with Grignard reagent have been used as key steps in the stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.170
• 作为产物：
  描述：

  (2S,3S)-1-(tert-butyldimethylsilyloxy)heptadecane-2,3-diol 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine

  摘要：

  The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide 9 with Grignard reagent have been used as key steps in the stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.170

文献信息

• Stereocontrolled synthesis of cytotoxic anhydrosphingosine pachastrissamine by using [3.3] sigmatropic rearrangement of allyl cyanate
  作者：Yoshiyasu Ichikawa、Kenshi Matsunaga、Toshiya Masuda、Hiyoshizo Kotsuki、Keiji Nakano

  DOI：10.1016/j.tet.2008.09.036

  日期：2008.12

  A new route for the synthesis of the cytotoxic anhydrosphingosine pachastrissamine has been developed. [3.3] Sigmatropic rearrangement of an allyl cyanate was employed to construct the allyl amine moiety in 2 from the chiral C-4 unit 3. Oxidative cleavage of the double bond in 2, followed by THF ring formation furnished the target pachastrissamine.

  已经开发了合成细胞毒性脱水鞘氨醇pachastrissamine的新途径。[3.3]烯丙基氰酸酯的σ迁移重排用于构造烯丙基胺部分在2从手性C-4单元3。2中双键的氧化裂解，然后形成THF环，提供了目标pachastrissamine。
• Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of l-xylo-[2R,3S,4S]-C18-phytosphingosine
  作者：Rodney A Fernandes、Pradeep Kumar

  DOI：10.1016/s0040-4039(00)01851-7

  日期：2000.12

  The first diastereoselective synthesis of L-xylo-(2R,3S 4S)-C-18-phytosphingosine (1) has been achieved by double stereodifferentiation of enantiomerically enriched terminal olefin 14 using (DHQD(2))-PHAL ligand in an asymmetric dihydroxylation with a diastereomeric ratio of 83:17. This phytosphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate 21. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine
  作者：G. Srinivas Rao、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2011.08.170

  日期：2011.11

  The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide 9 with Grignard reagent have been used as key steps in the stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine. (C) 2011 Elsevier Ltd. All rights reserved.