(R)-1-((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethane-1,2-diol | 325829-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethane-1,2-diol
• 英文别名: (1R)-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 325829-98-9
• 化学式: C₂₁H₄₂O₄
• 分子量: 358.562
• InChiKey: LHJPJJVYRFKHAU-AABGKKOBSA-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：

  (R)-1-((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethane-1,2-diol 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 氢气 、 三氯化铁 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 jaspine B
  参考文献：
  名称：

  Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]

  摘要：

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

  DOI：

  10.1021/jo0707838
• 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 (R)-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

• Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1021/jo0707838

  日期：2007.8.1

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of 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.