5-O-tert-butyldiphenylsilyl-L-arabinono-1,4-lactone | 156697-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-tert-butyldiphenylsilyl-L-arabinono-1,4-lactone
• 英文别名: 5-O-tert-butyldiphenylsilyl-L-arabino-1,4-lactone；(3R,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 156697-74-4
• 化学式: C₂₁H₂₆O₅Si
• 分子量: 386.52
• InChiKey: GVSOPBYAWJJMGA-GBESFXJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldiphenylsilyl-L-arabinono-1,4-lactone 在 吡啶 、 甲酸 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2-O-benzoyl-L-glycero-pent-2-enono-1,4-lactone
  参考文献：
  名称：

  β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms

  摘要：

  The well-known beta-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile beta-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).

  DOI：

  10.1016/0008-6215(95)00124-c
• 作为产物：
  描述：

  L-(+)-arabinose 在 咪唑 、 溴 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-O-tert-butyldiphenylsilyl-L-arabinono-1,4-lactone
  参考文献：
  名称：

  5-O-(叔丁基二苯基甲硅烷基)-2-脱氧-L-核糖内酯的快速合成

  摘要：

  摘要 描述了从 L-阿拉伯糖以 21% 的总产率方便地四步合成标题化合物 (1)。2-O-苯氧硫代羰基衍生物 6 的选择性形成及其在未受保护的羟基存在下进行的三丁基氢化锡/偶氮双（异丁腈）脱氧反应得到强调。

  DOI：

  10.1080/00397919408010201

文献信息

• β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms
  作者：Gerrit Limberg、Joachim Thiem

  DOI：10.1016/0008-6215(95)00124-c

  日期：1995.9

  The well-known beta-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile beta-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).
• Rapid Synthesis of 5-<i>O</i>-(<i>tert</i>-Butyldiphenylsilyl)-2-deoxy-<i>L</i>-ribonolactone
  作者：Rajiv Sharma、Victor E. Marquez

  DOI：10.1080/00397919408010201

  日期：1994.7

  Abstract A convenient, four-step synthesis of the title compound (1) in 21% overall yield from L-arabinose is described. Selective formation of the 2-O-phenoxythiocarbonyl derivative 6 and its tributyltin hydride/azobis(isobutyronitrile) deoxygenation performed in the presence of an unprotected hydroxyl group are highlighted.

  摘要 描述了从 L-阿拉伯糖以 21% 的总产率方便地四步合成标题化合物 (1)。2-O-苯氧硫代羰基衍生物 6 的选择性形成及其在未受保护的羟基存在下进行的三丁基氢化锡/偶氮双（异丁腈）脱氧反应得到强调。