(1S,2S,3S,5R)-2-(benzyloxy)-3-((S)-1,2-bis(benzyloxy)ethyl)-5-(((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)cyclopentan-1-ol | 1187445-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,5R)-2-(benzyloxy)-3-((S)-1,2-bis(benzyloxy)ethyl)-5-(((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)cyclopentan-1-ol
• CAS: 1187445-15-3
• 化学式: C₅₆H₆₂O₁₀
• 分子量: 895.102
• InChiKey: NOOBEJJPEMHNAO-ISKMJZKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.27
• 重原子数：
  66.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,5R)-2-(benzyloxy)-3-((S)-1,2-bis(benzyloxy)ethyl)-5-(((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)cyclopentan-1-ol 、 乙酸酐 以 吡啶 为溶剂， 反应 3.0h， 以99%的产率得到[(1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-phenylmethoxycyclopentyl] acetate
  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：

  3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose 在 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,2S,3S,5R)-2-(benzyloxy)-3-((S)-1,2-bis(benzyloxy)ethyl)-5-(((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)cyclopentan-1-ol
  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