[(2S,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxy-4-methyloxolan-3-yl] trifluoromethanesulfonate | 1227302-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxy-4-methyloxolan-3-yl] trifluoromethanesulfonate
• CAS: 1227302-22-8
• 化学式: C₁₂H₁₉F₃O₇S
• 分子量: 364.34
• InChiKey: BJNHXAMGCSZAKL-SPFKKGSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxy-4-methyloxolan-3-yl] trifluoromethanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以61.7 mg的产率得到[2S,3S,4S,5S,5(1R)]-3-azido-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran
  参考文献：
  名称：

  Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes

  摘要：

  A flexible strategy for the stereoselective synthesis of branched amino sugar analogues is described. It is based on a C-3-chain elongation of suitable protected aldoses. By using the sequence homoaldol reaction, epoxidation, and methanolysis alpha-methyl allo-furanosides are obtained. Proximate amination of the corresponding triflates afford the title compounds. All reactions proceed with high yield, high diastereoselectivities, and allow for a broad application.

  DOI：

  10.1055/s-0029-1218628
• 作为产物：
  描述：

  [2S,3R,4S,5S,5(1R)]-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran-3-ol 、 三氟甲磺酸酐 在 吡啶 作用下， 生成 [(2S,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxy-4-methyloxolan-3-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes

  摘要：

  A flexible strategy for the stereoselective synthesis of branched amino sugar analogues is described. It is based on a C-3-chain elongation of suitable protected aldoses. By using the sequence homoaldol reaction, epoxidation, and methanolysis alpha-methyl allo-furanosides are obtained. Proximate amination of the corresponding triflates afford the title compounds. All reactions proceed with high yield, high diastereoselectivities, and allow for a broad application.

  DOI：

  10.1055/s-0029-1218628