Methyl 4-Deoxy-4-fluoro-6-O-trityl-α-D-talopyranoside | 87586-11-6

• 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-talopyranoside
• 英文别名: (2S,3S,4R,5R,6R)-5-fluoro-2-methoxy-6-(trityloxymethyl)oxane-3,4-diol
• CAS: 87586-11-6
• 化学式: C₂₆H₂₇FO₅
• 分子量: 438.496
• InChiKey: HLTZCKHEKHGOJO-RYWAYVEBSA-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

• 作为反应物：
  描述：

  Methyl 4-Deoxy-4-fluoro-6-O-trityl-α-D-talopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl 3-O-acetyl-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
• 作为产物：
  描述：

  methyl 6-O-trityl-α-D-mannopyranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到Methyl 4-Deoxy-4-fluoro-6-O-trityl-α-D-talopyranoside
  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

• Intramolecular OH⋅⋅⋅FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF₂
  作者：Guy T. Giuffredi、Véronique Gouverneur、Bruno Bernet

  DOI：10.1002/anie.201303766

  日期：2013.9.27

  An intramolecular bifurcated H‐bond from the axial HO‐2 group to the axial F‐4 atom and to the O5 atom of α‐D‐hexopyranosides in apolar solvents is evidenced in 1H NMR spectra. The H‐accepting properties of the F atom are modulated by the orientation of the O‐substituent at the C3 atom and by an additional F atom at the C4 atom (see picture).

  在1 H NMR光谱中证实了分子内分叉的H键从轴向HO-2基团到轴向F-4原子以及α- D-己吡喃糖苷的O5原子。F原子的H接受特性受C3原子上O取代基的取向以及C4原子上另一个F原子的调控（见图）。
• Fluorinated carbohydrates. 2. Selective fluorination of gluco- and mannopyranosides. Use of 2-D NMR for structural assignments
  作者：Peter J. Card、Gade S. Reddy

  DOI：10.1021/jo00172a054

  日期：1983.12
• 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.