(1E,3R,4R,6R)-1-benzenesulfonyl-6-benzyloxy-1-N,N-diisopropylcarbamoyloxy-3-methyl nona-1,8-dien-4-ol | 405114-98-9

• 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: (1E,3R,4R,6R)-1-benzenesulfonyl-6-benzyloxy-1-N,N-diisopropylcarbamoyloxy-3-methyl nona-1,8-dien-4-ol
• 英文别名: [(1E,3R,4S,6R)-1-(benzenesulfonyl)-4-hydroxy-3-methyl-6-phenylmethoxynona-1,8-dienyl] N,N-di(propan-2-yl)carbamate
• CAS: 405114-98-9
• 化学式: C₃₀H₄₁NO₆S
• 分子量: 543.725
• InChiKey: NALOMGDPBJZZDN-XKCZMGTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1E,3R,4R,6R)-1-benzenesulfonyl-6-benzyloxy-1-N,N-diisopropylcarbamoyloxy-3-methyl nona-1,8-dien-4-ol 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.25h， 生成 (2S,4S,5S,6S(2R))-(6-(2-benzoyloxypent-4-enyl)-5-methyl-2-phenyl[1,3]dioxan-4-yl)carbaldehyde
  参考文献：
  名称：

  Diastereoselective Synthesis of Protected syn 1,3-Diols:  Preparation of the C16−C24 Portion of Dolabelides

  摘要：

  We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.

  DOI：

  10.1021/ol017122w
• 作为产物：
  描述：

  Diisopropyl-carbamic acid (Z)-(R)-6-benzyloxy-3-methyl-4-triethylsilanyloxy-nona-1,8-dienyl ester 在 ammonium heptamolybdate 四甲基乙二胺 、 双氧水 、 叔丁基锂 作用下， 以 乙醇 、 正己烷 、 水 、 正戊烷 为溶剂， 反应 20.0h， 生成 (1E,3R,4R,6R)-1-benzenesulfonyl-6-benzyloxy-1-N,N-diisopropylcarbamoyloxy-3-methyl nona-1,8-dien-4-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of Protected syn 1,3-Diols:  Preparation of the C16−C24 Portion of Dolabelides

  摘要：

  We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.

  DOI：

  10.1021/ol017122w

文献信息

• Diastereoselective Synthesis of Protected <i>s</i><i>yn</i> 1,3-Diols:  Preparation of the C16−C24 Portion of Dolabelides
  作者：Laurence Grimaud、Romain de Mesmay、Joëlle Prunet

  DOI：10.1021/ol017122w

  日期：2002.2.1

  We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.