methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate | 51433-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate
• CAS: 51433-20-6
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: KCNRGCYBEATHLU-JGFGOLAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate 在 正丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 10.25h， 生成 (E)-1-(4-methoxyphenyl)-2-(methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)ethylene
  参考文献：
  名称：

  Preparation of Sugar-Derived .beta.-Keto Phosphonates and Their Use in the Synthesis of Higher Sugars

  摘要：

  Sugar-derived beta-keto phosphonates 5, 6, 7, and 8 were synthesised by the acylation of lithium dimethyl methylphosphonate with the corresponding methyl glycuronates 1, 2, and 3 and glyconate 4 in THF at -78 degrees C, respectively. Wadsworth-Emmons reaction of 5, 6, 7, and 8 with various sugar-derived aldehydes proceeded in good yield to produce higher sugar enones. Similarly, C-2 symmetric bis phosphonate 28 derived from L-tartrate 27 was prepared and condensed with various sugar-derived aldehydes to provide C-2 symmetric bis enones in moderate yields. Treatment of the glucose-derived beta-keto phosphonate 5 with various aldehydes and excess Cs2CO3 resulted in complete cis elimination of the C-4 benzyl group along with the Wadsworth-Emmons reaction, leading to cross-conjugated dienones.

  DOI：

  10.1021/jo00100a047

文献信息

• Narkunan, K; Nagarajan, M, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 607 - 608
  作者：Narkunan, K、Nagarajan, M

  DOI：——

  日期：——