(4S,5S)-4-ethenyl-2,2-dimethyl-5-tetradecyl-1,3-dioxolane | 325829-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-4-ethenyl-2,2-dimethyl-5-tetradecyl-1,3-dioxolane
• CAS: 325829-96-7
• 化学式: C₂₁H₄₀O₂
• 分子量: 324.547
• InChiKey: BXLFGQIEQXWQOP-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-ethenyl-2,2-dimethyl-5-tetradecyl-1,3-dioxolane 在 4-二甲氨基吡啶 、 (DHQ)2-PHAL 吡啶 、 盐酸 、 四氧化锇 、 lithium aluminium tetrahydride 、 叠氮化锂 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (2S,3S,4S)-2-acetamidooctadecane-1,3,4-triyl triacetate
  参考文献：
  名称：

  Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of l-xylo-[2R,3S,4S]-C18-phytosphingosine

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)01851-7
• 作为产物：
  描述：

  (2R,3S)-2,3-dihydroxyheptadecanoic acid ethyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 2,2-DMP 、 sodium hexamethyldisilazane 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (4S,5S)-4-ethenyl-2,2-dimethyl-5-tetradecyl-1,3-dioxolane
  参考文献：
  名称：

  Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of l-xylo-[2R,3S,4S]-C18-phytosphingosine

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)01851-7

文献信息

• 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.