(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol | 471907-65-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol
• CAS: 471907-65-0
• 化学式: C₂₄H₄₂O₃
• 分子量: 378.596
• InChiKey: KJMMQUYOHCBKQR-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol 在 吡啶 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

  摘要：

  The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00201-x
• 作为产物：
  描述：

  [(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-ynyl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-yn-1-ol
  参考文献：
  名称：

  Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

  摘要：

  The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00201-x

文献信息

• Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine
  作者：Federica Compostella、Laura Franchini、Giovanni Battista Giovenzana、Luigi Panza、Davide Prosperi、Fiamma Ronchetti

  DOI：10.1016/s0957-4166(02)00201-x

  日期：2002.5

  The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.