(3R)-3-benzoyloxymethylisobenzofuranone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3R)-3-benzoyloxymethylisobenzofuranone
• 英文别名: [(1R)-3-oxo-1H-isobenzofuran-1-yl]methyl benzoate；[(1R)-3-oxo-1H-2-benzofuran-1-yl]methyl benzoate
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: QBLXCKOUNWURKQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-O-(S)-(2-ethenylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose 在 ruthenium trichloride 、 sodium periodate 、 对甲苯磺酸 、 溶剂黄146 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 叔丁醇 作用下， 以 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 生成 (3R)-3-benzoyloxymethylisobenzofuranone
  参考文献：
  名称：

  Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogues of α,β-butenolides

  摘要：

  Both enantiomers of 3-benzoyloxymethylisobenzofuranone have been obtained in good yield in six steps from phthalaldehyde using a D-xylose derivative as a chiral protecting group. The two chiral heterocycles are gamma-hydroxymethyl-alpha,beta-butenolide analogues having a benzene ring in positions 2 and 3. The key step was the dihydroxylation using both OsO4 and AD-mix developed by Sharpless. The asymmetric dihydroxylation using AD-mix required a double diastereoselectivity and gave excellent diastereoisomeric excess. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02662-x

文献信息

• Enantiomerical excess determination, purification and biological evaluation of (3S) and (3R) α,β-butenolide analogues of isobenzofuranone
  作者：Emmanuelle Lipka、Marie-Pierre Vaccher、Claude Vaccher、Christophe Len

  DOI：10.1016/j.bmcl.2004.11.065

  日期：2005.2

  The asymmetric synthesis of isobenzofurane analogues, new potential antiviral agents, is reported. High performance liquid chromatography (HPLC) was the technique chosen to separate the enantiomers. We describe this chiral separation and then determine the enantiomerical excess. The biological results of each tested enantiomer are given.

  据报道，新的潜在抗病毒药物异苯并呋喃类似物的不对称合成。高效液相色谱（HPLC）是选择用于分离对映异构体的技术。我们描述这种手性分离，然后确定对映体过量。给出了每种测试对映体的生物学结果。
• Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogues of α,β-butenolides
  作者：Christophe Len、Abdelmajid Sélouane、Asa Weiling、Fabien Coicou、Denis Postel

  DOI：10.1016/s0040-4039(02)02662-x

  日期：2003.1

  Both enantiomers of 3-benzoyloxymethylisobenzofuranone have been obtained in good yield in six steps from phthalaldehyde using a D-xylose derivative as a chiral protecting group. The two chiral heterocycles are gamma-hydroxymethyl-alpha,beta-butenolide analogues having a benzene ring in positions 2 and 3. The key step was the dihydroxylation using both OsO4 and AD-mix developed by Sharpless. The asymmetric dihydroxylation using AD-mix required a double diastereoselectivity and gave excellent diastereoisomeric excess. (C) 2003 Elsevier Science Ltd. All rights reserved.