[(E,2S,3R)-2-azido-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxyoctadec-4-en-3-yl] benzoate | 335596-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(E,2S,3R)-2-azido-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxyoctadec-4-en-3-yl] benzoate
• CAS: 335596-01-5
• 化学式: C₃₃H₅₇N₃O₃Si
• 分子量: 571.919
• InChiKey: NPSMSDFBHPGZEH-MQBRABDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.81
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(E,2S,3R)-2-azido-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxyoctadec-4-en-3-yl] benzoate 在 氢氟酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以85%的产率得到(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-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
• 作为产物：
  描述：

  (2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 [(E,2S,3R)-2-azido-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxyoctadec-4-en-3-yl] benzoate
  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.