[(1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-[(2-methylpropan-2-yl)oxy]-2-phenylmethoxycyclopentyl] acetate | 1187445-19-7

• 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: [(1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-[(2-methylpropan-2-yl)oxy]-2-phenylmethoxycyclopentyl] acetate
• CAS: 1187445-19-7
• 化学式: C₃₄H₄₂O₆
• 分子量: 546.704
• InChiKey: OTOBUXHYXARRIO-MPJBSJSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,4S,5S,6R)-1,2,4-tri-O-benzyl-5,6-di-O-acetyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 54.0h， 生成 [(1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-[(2-methylpropan-2-yl)oxy]-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

文献信息

• Synthesis of carbadisaccharide mimics of galactofuranosides
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2009.06.115

  日期：2009.9

  A partially protected carbagalactofuranose was converted into a 1,2-anhydro derivative. This epoxide was opened with alcohol nucleophiles under Lewis acid catalysis to give beta-carbagalactofuranose pseudodisaccharides with excellent regioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.