(2S,3R)-2,3-O-isopropylidene-6-pivaloyloxyhexanoic acid | 864948-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-2,3-O-isopropylidene-6-pivaloyloxyhexanoic acid
• 英文别名: (4S,5R)-5-[3-(2,2-dimethylpropanoyloxy)propyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 864948-08-3
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: SVNXZYKXKBMXLZ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-O-isopropylidene-6-pivaloyloxyhexanoic acid 在 草酰氯 、 三氟化硼乙醚 、 碘 、 叔丁基锂 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 乙醚 、 正己烷 、 正庚烷 、 二氯甲烷 为溶剂， 反应 8.42h， 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：

  4-pivaloyloxybutanal 在 氢氧化钾 、 甲基磺酰胺 、 AD-mix-β 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 7.0h， 生成 (2S,3R)-2,3-O-isopropylidene-6-pivaloyloxyhexanoic acid
  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.