(4R,5R,6S)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-2-one | 847659-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R,6S)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-2-one
• CAS: 847659-83-0
• 化学式: C₁₂H₂₃N₃O₃Si
• 分子量: 285.418
• InChiKey: UFSXLALVLPLUPS-NGZCFLSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-2-one 在 四丁基氟化铵 、 二异丁基氢化铝 作用下， 生成 (2S,4R,5R,6S)-4-azido-6-methyloxane-2,5-diol
  参考文献：
  名称：

  A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring-closing metathesis

  摘要：

  A systematic synthetic strategy has been developed for producing uncommon sugars. This method involved kinetic resolution allylic alcohol followed by ring-closing-metathesis (RCM) to generate optical pure lactones as the common precursors. After further derivatization, four representative uncommon sugar units were successfully synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.014
• 作为产物：
  描述：

  4-O-acetyl-2,3,6-trideoxy-L-erythro-hex-2-enono-1,5-lactone 在 吡啶 、 咪唑 、 sodium hypochlorite 、 sodium tetrahydroborate 、 二苯基二硒醚 、 potassium carbonate 、 异丙醇 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (4R,5R,6S)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-2-one
  参考文献：
  名称：

  A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal

  摘要：

  An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-L-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3-OEt2-induced peroxidation of rhamnal to construct key intermediate alpha,beta-unsaturated lactone as the common precursor. After further derivatization, four 3-azido hexoses were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.062