3-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]propanal | 864948-12-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]propanal
• CAS: 864948-12-9
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: UAOQSAICRWDXSP-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]propanal 在 咪唑 、 叔丁基锂 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 tert-Butyl-{(S)-1-[2-((4R,5R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl]-3-methyl-but-2-enyloxy}-diphenyl-silane
  参考文献：
  名称：

  Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues

  摘要：

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.

  DOI：

  10.1021/jo050888f
• 作为产物：
  描述：

  3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 3-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]propanal
  参考文献：
  名称：

  Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues

  摘要：

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.

  DOI：

  10.1021/jo050888f

文献信息

• Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues
  作者：Fatoumata Camara、Johana Angarita、David R. Mootoo

  DOI：10.1021/jo050888f

  日期：2005.8.1

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.