methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-α-D-mannopyranoside | 1332832-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-α-D-mannopyranoside
• CAS: 1332832-46-8
• 化学式: C₁₉H₂₇FO₆
• 分子量: 370.418
• InChiKey: STBWOVFQGCSVNH-JJTUDDRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-α-D-mannopyranoside 在 吡啶 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -15.0~60.0 ℃ 、101.33 kPa 条件下， 反应 11.25h， 生成 methyl 2,4-dideoxy-2,4-difluoro-6-O-pivaloyl-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
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 水 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-α-D-mannopyranoside 、 3-O-benzyl-2-deoxy-2-fluoro-4,6-di-O-pivaloyl-α-D-mannopyranoside
  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