ethyl 2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,4R,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl(hydroxy)methyl]acrylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,4R,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl(hydroxy)methyl]acrylate
• 英文别名: ethyl 2-[[(3aR,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-hydroxymethyl]prop-2-enoate
• 化学式: C₁₈H₂₈O₈
• 分子量: 372.416
• InChiKey: ALAPOJARDWMDIP-TWBDHPCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,4R,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl(hydroxy)methyl]acrylate 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以45%的产率得到1-[6-[2,2-dimethyl-(4R)-dioxolan-4-yl]-2,2-dimethyl-(3aR,4R,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]-2-methylene-1,3-propanediol
  参考文献：
  名称：

  Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes

  摘要：

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.026
• 作为产物：
  描述：

  丙烯酸乙酯 、 2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose 在 三乙烯二胺 作用下， 以 环丁砜 为溶剂， 反应 15.0h， 以85%的产率得到ethyl 2-[6-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,4R,6R,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl(hydroxy)methyl]acrylate
  参考文献：
  名称：

  Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes

  摘要：

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.026

文献信息

• Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan

  DOI：10.1016/j.tetasy.2005.06.026

  日期：2005.8

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.