(4S)-4-[(1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-chloro-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxan-5-one | 1446852-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-[(1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-chloro-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxan-5-one
• CAS: 1446852-35-2
• 化学式: C₁₅H₂₉ClO₅Si
• 分子量: 352.931
• InChiKey: KRKQGHAQEHULNK-KGYLQXTDSA-N

物化性质

• 沸点：
  415.2±45.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-[(1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-chloro-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxan-5-one 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 水 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以78%的产率得到1-deoxy-β-D-psicosofuranose
  参考文献：
  名称：

  A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis

  摘要：

  A tandem, proline-catalyzed alpha-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of alpha-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

  DOI：

  10.1021/ol401370b
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 2,2-二甲基-1,3-二恶烷-5-酮 在 N-氯代丁二酰亚胺 、 L-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以49%的产率得到(4S)-4-[(1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-chloro-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxan-5-one
  参考文献：
  名称：

  A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis

  摘要：

  A tandem, proline-catalyzed alpha-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of alpha-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

  DOI：

  10.1021/ol401370b

文献信息

• A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis
  作者：Milan Bergeron-Brlek、Timothy Teoh、Robert Britton

  DOI：10.1021/ol401370b

  日期：2013.7.19

  A tandem, proline-catalyzed alpha-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of alpha-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.