3-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-propan-1-ol | 864948-21-0

• 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)-propan-1-ol
• 英文别名: 3-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]propan-1-ol
• CAS: 864948-21-0
• 化学式: C₁₄H₂₀O₃S
• 分子量: 268.377
• InChiKey: BKNQXBULKOWZAI-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64
• 氢给体数：
  1
• 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)-propan-1-ol 在 草酰氯 、 叔丁基锂 、 二甲基亚砜 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.42h， 生成 1-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-5-methylhex-4-en-3-ol
  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：

  methyl (E)-6-pivaloyloxy-2-hexenoate 在 氢氧化钾 、 甲基磺酰胺 、 AD-mix-β 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 碘 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 10.0h， 生成 3-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-propan-1-ol
  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.