methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-idopyranoside | 1332832-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-idopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-5-fluoro-2-methoxy-6-(trityloxymethyl)oxane-3,4-diol
• CAS: 1332832-39-9
• 化学式: C₂₆H₂₇FO₅
• 分子量: 438.496
• InChiKey: HLTZCKHEKHGOJO-KJWQXZETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4-deoxy-4-fluoro-3-O-trifluoromethanesulfonyl-6-O-trityl-α-D-talopyranoside 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-idopyranoside
  参考文献：
  名称：

  Facile synthesis of 4-deoxy-4-fluoro-α-d-talopyranoside, 4-deoxy-4-fluoro-α-d-idopyranoside and 2,4-dideoxy-2,4-difluoro-α-d-talopyranoside

  摘要：

  The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-alpha--talopyranoside served as a precursor to 4-deoxy-4-fluoro-alpha-D-idopyranoside, allowing for inversion of configuration at C-3 via a three-step protocol. The synthesis of 2,4-dideoxy-2,4-difluoro-alpha-D-talopyranoside is based on two nucleophilic fluorination events at C-2 then at C-4 using TBAF center dot 3H(2)O and TBAF.4tBuOH as a fluoride source. All compounds are prepared as pure stereoisomers and are therefore suitable probes for OH center dot center dot center dot F H-bonding studies by (1)H NMR spectroscopy. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.05.017

文献信息

• Facile synthesis of 4-deoxy-4-fluoro-α-d-talopyranoside, 4-deoxy-4-fluoro-α-d-idopyranoside and 2,4-dideoxy-2,4-difluoro-α-d-talopyranoside
  作者：Guy T. Giuffredi、Laura E. Jennings、Bruno Bernet、Véronique Gouverneur

  DOI：10.1016/j.jfluchem.2011.05.017

  日期：2011.10

  The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-alpha--talopyranoside served as a precursor to 4-deoxy-4-fluoro-alpha-D-idopyranoside, allowing for inversion of configuration at C-3 via a three-step protocol. The synthesis of 2,4-dideoxy-2,4-difluoro-alpha-D-talopyranoside is based on two nucleophilic fluorination events at C-2 then at C-4 using TBAF center dot 3H(2)O and TBAF.4tBuOH as a fluoride source. All compounds are prepared as pure stereoisomers and are therefore suitable probes for OH center dot center dot center dot F H-bonding studies by (1)H NMR spectroscopy. (C) 2011 Elsevier B.V. All rights reserved.