2,2-Dimethyl-propionic acid (R)-2-azido-2-((4S,5S)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl ester | 325830-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (R)-2-azido-2-((4S,5S)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl ester
• 英文别名: [(2R)-2-azido-2-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethyl] 2,2-dimethylpropanoate
• CAS: 325830-03-3
• 化学式: C₂₆H₄₉N₃O₄
• 分子量: 467.693
• InChiKey: LMRZFLUDISYCBN-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  33.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (R)-2-azido-2-((4S,5S)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以96%的产率得到(R)-2-Amino-2-((4S,5S)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethanol
  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 4-二甲氨基吡啶 、 (DHQ)2-PHAL 吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 叠氮化锂 、 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 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 48.0h， 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

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.