(2R,3S,4R,6R)-2-[(2S)-butan-2-yl]-6-(hydroxymethyl)-3-methyloxan-4-ol | 1063967-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3S,4R,6R)-2-[(2S)-butan-2-yl]-6-(hydroxymethyl)-3-methyloxan-4-ol
• CAS: 1063967-54-3
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: JJQVSIMTVAAXSE-FBDQPXRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,6R)-2-[(2S)-butan-2-yl]-6-(hydroxymethyl)-3-methyloxan-4-ol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到(2R,3S,4R,6R)-2-((S)-sec-butyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyltetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of basiliskamides A and B via Prins cyclisation

  摘要：

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.024
• 作为产物：
  描述：

  (S)-2-甲基丁醛 、 (E)-(R)-Hex-4-ene-1,2-diol 在 三氟乙酸 、 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以50%的产率得到(2R,3S,4R,6R)-2-[(2S)-butan-2-yl]-6-(hydroxymethyl)-3-methyloxan-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of basiliskamides A and B via Prins cyclisation

  摘要：

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.024

文献信息

• Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.07.024

  日期：2008.9

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.