(2R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-yn-2-ol | 290343-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-yn-2-ol
• CAS: 290343-20-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: XMPDUFJJAXWNDO-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-yn-2-ol 在 15-冠醚-5 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 甲醇 为溶剂， 生成 (2S,4R)-4-methoxyhept-6-yne-1,2-diol
  参考文献：
  名称：

  Stereoselective synthesis of substituted ketopyranose subunits of polyketide natural products by intramolecular alkoxycarbonylation of δ-alkynyl alcohols

  摘要：

  Upon treatment with 5 mol% Pd(MeCN)(2)Cl-2 in methanol containing 1.1-1.5 equiv. of p-benzoquinone under 1 atm of CO, delta-hydroxy alkynes are converted to methyl ketopyranosides with excellent stereoselectivity. The reaction proceeds by sequential intramolecular alkoxypalladation of the alkyne followed by CO insertion and methanolysis, then an ensuing Pd+2-catalyzed 1,4-addition of methanol to the intermediate conjugated ester. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00705-x
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以120 mg的产率得到(2R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-yn-2-ol
  参考文献：
  名称：

  A macrolactonisation approach to the cembrane carbocycle of bielschowskysin

  摘要：

  By judicious choice of a conformationally constraining unit to predispose cyclisation to a 15-membered ring, we present a straightforward strategy to a cembranolide precursor of bielschowskysin by the Sonogashira coupling of two readily prepared fragments (from D-glucose and L-malic acid) followed by a facile beta-acylketene macrolactonisation reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.012

文献信息

• A macrolactonisation approach to the cembrane carbocycle of bielschowskysin
  作者：Eugene G. Yang、Karthik Sekar、Martin J. Lear

  DOI：10.1016/j.tetlet.2013.06.012

  日期：2013.8

  By judicious choice of a conformationally constraining unit to predispose cyclisation to a 15-membered ring, we present a straightforward strategy to a cembranolide precursor of bielschowskysin by the Sonogashira coupling of two readily prepared fragments (from D-glucose and L-malic acid) followed by a facile beta-acylketene macrolactonisation reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of substituted ketopyranose subunits of polyketide natural products by intramolecular alkoxycarbonylation of δ-alkynyl alcohols
  作者：James A. Marshall、Mathew M. Yanik

  DOI：10.1016/s0040-4039(00)00705-x

  日期：2000.6

  Upon treatment with 5 mol% Pd(MeCN)(2)Cl-2 in methanol containing 1.1-1.5 equiv. of p-benzoquinone under 1 atm of CO, delta-hydroxy alkynes are converted to methyl ketopyranosides with excellent stereoselectivity. The reaction proceeds by sequential intramolecular alkoxypalladation of the alkyne followed by CO insertion and methanolysis, then an ensuing Pd+2-catalyzed 1,4-addition of methanol to the intermediate conjugated ester. (C) 2000 Elsevier Science Ltd. All rights reserved.