[(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-ynyl] acetate | 471907-68-3

• 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-ynyl] acetate
• CAS: 471907-68-3
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: FHRDCPIIRLAVPN-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-ynyl] acetate 在 吡啶 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 (2R,3R,4E)-1,2-O-cyclohexylidene-4-octadecene-1,2,3-triol
  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：

  乙酸乙烯酯 、 1-十五炔 、 (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 乙基溴化镁 、 Candida antarctica lipase 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 1.0h， 生成 (2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol 、 [(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadec-2-ynyl] acetate
  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