(+)-N,N'-(2-oxopropane-1,3-diyl)bis[(2R)-3-(tert-butyldiphenylsilyloxy)-2-hydroxypropanamide] | 949087-14-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+)-N,N'-(2-oxopropane-1,3-diyl)bis[(2R)-3-(tert-butyldiphenylsilyloxy)-2-hydroxypropanamide]
• 英文别名: (2R)-3-[tert-butyl(diphenyl)silyl]oxy-N-[3-[[(2R)-3-[tert-butyl(diphenyl)silyl]oxy-2-hydroxypropanoyl]amino]-2-oxopropyl]-2-hydroxypropanamide
• CAS: 949087-14-3
• 化学式: C₄₁H₅₂N₂O₇Si₂
• 分子量: 741.044
• InChiKey: OQAQJNLHBJVFHJ-FZNHDDJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  52
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-N,N'-(2-oxopropane-1,3-diyl)bis[(2R)-3-(tert-butyldiphenylsilyloxy)-2-hydroxypropanamide] 在 对甲苯磺酸 作用下， 以 正丁醇 、 甲苯 为溶剂， 反应 13.0h， 以57%的产率得到(-)-(2R)-3-(tert-butyldiphenylsilyloxy)-2-hydroxy-N-({(2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-3-oxo-2,3-dihydro-2H-1,4-oxazin-6-yl}methyl)propanamide
  参考文献：
  名称：

  Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

  摘要：

  Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5] undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1] octan-2-one 18 or to the oxazinone 32 in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.109
• 作为产物：
  描述：

  (-)-methyl-(2R)-3-(tert-butyldiphenylsilyloxy)-2-hyrdoxypropanoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 三甲基溴硅烷 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+)-N,N'-(2-oxopropane-1,3-diyl)bis[(2R)-3-(tert-butyldiphenylsilyloxy)-2-hydroxypropanamide]
  参考文献：
  名称：

  Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

  摘要：

  Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5] undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1] octan-2-one 18 or to the oxazinone 32 in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.109

文献信息

• Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks
  作者：Marlène Goubert、Loïc Toupet、Marie-Eve Sinibaldi、Isabelle Canet

  DOI：10.1016/j.tet.2007.05.109

  日期：2007.8

  Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5] undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1] octan-2-one 18 or to the oxazinone 32 in good yields. (c) 2007 Elsevier Ltd. All rights reserved.