ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate | 236739-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate
• CAS: 236739-66-5
• 化学式: C₄₂H₄₆O₁₁
• 分子量: 726.821
• InChiKey: YIFDUCUOSSXTIB-UPMJLWDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  125.05
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到ethyl acetoxy(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate
  参考文献：
  名称：

  Alkylidenation of Sugar Lactones and Further Transformation toC-Glycosides

  摘要：

  The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar delta-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated beta-C-glycosides and amino beta-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino beta-C-glycosides. Other transformation of the enol ether function is also reported.

  DOI：

  10.1080/07328309908544013
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-吡喃半乳糖 在 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 45.0h， 生成 ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate
  参考文献：
  名称：

  Alkylidenation of Sugar Lactones and Further Transformation toC-Glycosides

  摘要：

  The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar delta-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated beta-C-glycosides and amino beta-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino beta-C-glycosides. Other transformation of the enol ether function is also reported.

  DOI：

  10.1080/07328309908544013