(2R)-3-(tert-butyldiphenylsilyloxy)-2-(methoxymethoxy)propanoyl chloride | 949087-10-9

• 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: (2R)-3-(tert-butyldiphenylsilyloxy)-2-(methoxymethoxy)propanoyl chloride
• 英文别名: (2R)-3-[tert-butyl(diphenyl)silyl]oxy-2-(methoxymethoxy)propanoyl chloride
• CAS: 949087-10-9
• 化学式: C₂₁H₂₇ClO₄Si
• 分子量: 406.981
• InChiKey: DHJFIHFKVKATGT-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-3-(tert-butyldiphenylsilyloxy)-2-(methoxymethoxy)propanoyl chloride 在 4-二甲氨基吡啶 、 三甲基溴硅烷 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 33.0h， 生成 (-)-(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 、 lithium hydroxide 、 草酰氯 、 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 26.0h， 生成 (2R)-3-(tert-butyldiphenylsilyloxy)-2-(methoxymethoxy)propanoyl chloride
  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.