(1R,2S,3S)-4-((S)-1,2-diacetoxyethyl)cyclopent-4-ene-1,2,3-triyl triacetate | 1314871-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3S)-4-((S)-1,2-diacetoxyethyl)cyclopent-4-ene-1,2,3-triyl triacetate
• CAS: 1314871-75-4
• 化学式: C₁₇H₂₂O₁₀
• 分子量: 386.356
• InChiKey: PKHCLWOKYSQASO-NCOADZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S)-4-((S)-1,2-diacetoxyethyl)cyclopent-4-ene-1,2,3-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到(1R,2S,3S)-4-[(1S)-1,2-dihydroxyethyl]cyclopent-4-ene-1,2,3-triol
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032
• 作为产物：
  描述：

  (2S,4S,5S,6R)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-3-methyleneoct-7-ene-1,2,4,5,6-pentaol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 氨 、 sodium methylate 、 sodium 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 88.33h， 生成 (1R,2S,3S)-4-((S)-1,2-diacetoxyethyl)cyclopent-4-ene-1,2,3-triyl triacetate
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032