(4S,5S)-5-hydroxymethyl-4-C-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one | 136265-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5S)-5-hydroxymethyl-4-C-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one
• 英文别名: (4S,5S)-5-hydroxymethyl-4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one；(4S,5S)-5-hydroxymethyl-4(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one；(4S,5S)-5-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)oxolan-2-one
• CAS: 136265-74-2
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: WLMGSCAOKIIWJV-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-hydroxymethyl-4-C-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one 在 吡啶 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 (4S,5S)-5-benzoyloxymethyl-4-isopropenyltetrahydrofuran-2-one
  参考文献：
  名称：

  A new approach to cis -chrysanthemic acid

  摘要：

  DOI：

  10.1016/0008-6215(92)84186-v
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 、 异丙醇 反应 48.0h， 以94%的产率得到(4S,5S)-5-hydroxymethyl-4-C-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  A new approach to cis -chrysanthemic acid

  摘要：

  DOI：

  10.1016/0008-6215(92)84186-v

文献信息

• Convenient Synthesis of 4-<i>C</i>-Branched Lactones and 3′-<i>C</i>-Branched 2′,3′-Dideoxynucleosides
  作者：Jesper Wengel、Kirsten Østergaard、Anders Hager

  DOI：10.1080/07328319608002436

  日期：1996.7

  The regio- and stereoselective photocatalysed addition of 2-propanol and cyclopentanol to (5S)-hydroxymethylfuran-2(5H)-one (1) gave 4-C-branched lactones 2 and 3 after selective silylations. The lactones 2 and 3 were radically deoxygenated affording lactones 4 and 5, respectively. As an example, compound 2 was transformed without purification of the intermediates into an anomeric mixtures of deprotected 3'-C-branched 2',3'-dideoxynucleosides 6 by the following reaction sequence: silylation, reduction, acetylation, coupling with silylated thymine and desilylation.
• Mann, John; Weymouth-Wilson, Alexander C., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3141 - 3148
  作者：Mann, John、Weymouth-Wilson, Alexander C.

  DOI：——

  日期：——