(R)-1-(2-furyl)-2-O-benzyl-1,2-ethanediol | 63802-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(2-furyl)-2-O-benzyl-1,2-ethanediol
• 英文别名: (R)-2-(benzyloxy)-1-(furan-2-yl)ethanol；S-2-<1-(2-O-Benzyl-1,2-dihydroxyethyl)>furan；(1R)-1-(furan-2-yl)-2-phenylmethoxyethanol
• CAS: 63802-97-1
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: PMMCEEQCQTZJSX-GFCCVEGCSA-N

物化性质

• 沸点：
  318.5±32.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(2-furyl)-2-O-benzyl-1,2-ethanediol 在 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 水合氯化铈 、 Na⁽¹⁺⁾*CHO₃^(1-)*3H₂O 、 sodium acetate 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides

  摘要：

  An approach has been developed of the regioselective methylation of alpha-(1 -> 4)-linked mannopyranose oligosaccharides via a four-step methodology. The key reaction involved n-Bu2SnCl2-mediated activation of cis-diols. By tuning protecting groups on the substrates, multiple cis-diols in the substrates were functionalized in a consistent and regioselective manner. Using optimized substrates and reaction conditions, regioselective methylation of di-, tri-, and tetrasaccharide substrates proceeded in isolated yields per cis-diol of 95, 88 and 79%, respectively. The methodology was also applied to functionalize trans-diols in alpha-cyclodextrin.

  DOI：

  10.1021/jo4001299
• 作为产物：
  描述：

  2-呋喃甲基乙酯 在 2,3,5-三甲基吡啶 、 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 sodium tetrahydroborate 、 4 A molecular sieve 、 四丁基氟化铵 、 四丁基溴化铵 、 二异丁基氢化铝 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 (R)-1-(2-furyl)-2-O-benzyl-1,2-ethanediol
  参考文献：
  名称：

  A short route to homochiral D- and L-hexose precursors from (R)-methyl-p-tolylsulfoxide

  摘要：

  Homochiral D- and L-hexose precursors have been prepared in good overall yield from (R)-methyl-p-tolysulfoxide as the sole asymmetric inductor. The process involves sequential condensation of the sulfoxide with ethyl 2-furancarboxylate, stereoselective sulfoxide-monitored carbonyl reduction, Pummerer rearrangement of the sulfinyl group, reduction of the resulting aldehydes and ring-oxidation of the corresponding furfuryl alcohols.

  DOI：

  10.1016/0957-4166(94)80033-2

文献信息

• Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides
  作者：Li Xia、Todd L. Lowary

  DOI：10.1021/jo4001299

  日期：2013.4.5

  An approach has been developed of the regioselective methylation of alpha-(1 -> 4)-linked mannopyranose oligosaccharides via a four-step methodology. The key reaction involved n-Bu2SnCl2-mediated activation of cis-diols. By tuning protecting groups on the substrates, multiple cis-diols in the substrates were functionalized in a consistent and regioselective manner. Using optimized substrates and reaction conditions, regioselective methylation of di-, tri-, and tetrasaccharide substrates proceeded in isolated yields per cis-diol of 95, 88 and 79%, respectively. The methodology was also applied to functionalize trans-diols in alpha-cyclodextrin.
• A short route to homochiral D- and L-hexose precursors from (R)-methyl-p-tolylsulfoxide
  作者：José-Manuel Llera、Mariana Trujillo、María-Eugenia Blanco、Felipe Alcudia

  DOI：10.1016/0957-4166(94)80033-2

  日期：1994.4

  Homochiral D- and L-hexose precursors have been prepared in good overall yield from (R)-methyl-p-tolysulfoxide as the sole asymmetric inductor. The process involves sequential condensation of the sulfoxide with ethyl 2-furancarboxylate, stereoselective sulfoxide-monitored carbonyl reduction, Pummerer rearrangement of the sulfinyl group, reduction of the resulting aldehydes and ring-oxidation of the corresponding furfuryl alcohols.