methyl 5-deoxy-5-iodo-D-lyxofuranoside | 63029-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-5-iodo-D-lyxofuranoside
• CAS: 63029-11-8
• 化学式: C₆H₁₁IO₄
• 分子量: 274.055
• InChiKey: WYMYPTFVMQUWRR-VANKVMQKSA-N

物化性质

• 沸点：
  367.3±42.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-5-iodo-D-lyxofuranoside 在 ammonium acetate 、 氨 、 sodium cyanoborohydride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 (2R,3S)-1-aminopent-4-ene-2,3-diol
  参考文献：
  名称：

  A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

  摘要：

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.016
• 作为产物：
  描述：

  methyl-α-D-lyxofuranoside 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到methyl 5-deoxy-5-iodo-D-lyxofuranoside
  参考文献：
  名称：

  A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

  摘要：

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.016