methyl 4-acetamido-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 4-acetamido-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside
• 英文别名: N-[2-(difluoromethyl)-6-methoxyoxan-3-yl]acetamide
• 化学式: C₉H₁₅F₂NO₃
• 分子量: 223.22
• InChiKey: ASBRKKXKTIMYAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 6,6-difluoro-4-nitro-2,3,4,6-tetradeoxyhexapyranoside 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 methyl 4-acetamido-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside
  参考文献：
  名称：

  A remarkably simple route to versatile difluoromethylated molecules

  摘要：

  Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds. Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and beta-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.

  DOI：

  10.1021/jo00060a055

文献信息

• A remarkably simple route to versatile difluoromethylated molecules
  作者：Sadanori Kaneko、Takashi Yamazaki、Tomoya Kitazume

  DOI：10.1021/jo00060a055

  日期：1993.4

  Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds. Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and beta-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.