[(2R,3S,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl ethyl carbonate | 314249-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [(2R,3S,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl ethyl carbonate
• CAS: 314249-22-4
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: SVEHRNJYVKAVDJ-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl ethyl carbonate 、 苯甲醇 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以65%的产率得到(2S,4R,5S,6R)-2-Benzyloxy-4,5-dimethoxy-6-methoxymethyl-3-methylene-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals

  摘要：

  C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00775-4
• 作为产物：
  描述：

  氯甲酸乙酯 、 ((4R,5S,6R)-4,5-Dimethoxy-6-methoxymethyl-5,6-dihydro-4H-pyran-3-yl)-methanol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以65%的产率得到[(2R,3S,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl ethyl carbonate
  参考文献：
  名称：

  Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals

  摘要：

  C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00775-4

文献信息

• Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals
  作者：Anuradha Gupta、Yashwant D. Vankar

  DOI：10.1016/s0040-4020(00)00775-4

  日期：2000.10

  C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.