(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(1-hydroxycyclopentyl)oxolan-2-one | 181182-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(1-hydroxycyclopentyl)oxolan-2-one
• CAS: 181182-61-6
• 化学式: C₂₆H₃₄O₄Si
• 分子量: 438.639
• InChiKey: ADMOSJUFAMBZGO-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(1-hydroxycyclopentyl)oxolan-2-one 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 22.5h， 生成 (4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-cyclopentyloxolan-2-one
  参考文献：
  名称：

  Convenient Synthesis of 4-C-Branched Lactones and 3′-C-Branched 2′,3′-Dideoxynucleosides

  摘要：

  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.

  DOI：

  10.1080/07328319608002436
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 在 咪唑 、 苯乙酮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(1-hydroxycyclopentyl)oxolan-2-one
  参考文献：
  名称：

  Convenient Synthesis of 4-C-Branched Lactones and 3′-C-Branched 2′,3′-Dideoxynucleosides

  摘要：

  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.

  DOI：

  10.1080/07328319608002436