(5R)-4-benzyloxy-5-(triphenylmethoxy)methyl-[5H]furan-2-one | 150186-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (5R)-4-benzyloxy-5-(triphenylmethoxy)methyl-[5H]furan-2-one
• 英文别名: (2R)-3-phenylmethoxy-2-(trityloxymethyl)-2H-furan-5-one
• CAS: 150186-51-9
• 化学式: C₃₁H₂₆O₄
• 分子量: 462.545
• InChiKey: SXSBKYAVIKUGEC-GDLZYMKVSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  644.3±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-4-benzyloxy-5-(triphenylmethoxy)methyl-[5H]furan-2-one 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 67.0h， 生成 3-十六烷酰基-5-羟甲基tetronic酸
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 1.07h， 以347 mg的产率得到(5R)-4-benzyloxy-5-(triphenylmethoxy)methyl-[5H]furan-2-one
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i

文献信息

• Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins
  作者：Rainer Schobert、Carsten Jagusch

  DOI：10.1021/jo050797i

  日期：2005.7.1

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.