(2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol | 335595-99-8

• 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: (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol
• 英文别名: [(E,2R,3R)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-2-hydroxyoctadec-4-en-3-yl] benzoate
• CAS: 335595-99-8
• 化学式: C₃₃H₅₈O₄Si
• 分子量: 546.907
• InChiKey: XXGVAXFJDGNVNC-FFFUTZAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  38
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol 在 sodium azide 、 氢氟酸 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 (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 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-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

• A short and practical route to 3-O-benzoyl azidosphingosine
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0008-6215(00)00323-2

  日期：2001.3

  A short and practical route to 3-O-benzoyl azidosphingosine from D-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary

  描述了从D-木糖制备3-O-苯甲酰基叠氮鞘氨醇的短而实用的途径。合成过程避免使用昂贵和危险的化学药品（例如汞盐），并且可重现至少20 g的规模。此外，通过利用伯基二甲基甲硅烷基氯对伯HO-1进行区域选择性保护，合成以最少的保护基团操作进行到3-O-苯甲酰基叠氮基鞘氨醇。
• 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.