(S)-1-((4S,5S)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol | 325830-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((4S,5S)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol
• 英文别名: (1S)-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 325830-00-0
• 化学式: C₂₁H₄₂O₄
• 分子量: 358.562
• InChiKey: LHJPJJVYRFKHAU-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (S)-1-((4S,5S)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol 在 4-二甲氨基吡啶 吡啶 、 叠氮化锂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,2-Dimethyl-propionic acid (R)-2-azido-2-((4S,5S)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl ester
  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 (DHQ)2-PHAL 四氧化锇 、 lithium aluminium tetrahydride 、 草酰氯 、 2,2-DMP 、 sodium hexamethyldisilazane 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 36.0h， 生成 (S)-1-((4S,5S)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol
  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.