(2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate | 1293921-68-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate
• CAS: 1293921-68-2
• 化学式: C₂₉H₄₇NO₁₀SSi
• 分子量: 629.844
• InChiKey: GRUOTWNVHRDAMF-MBWGTIHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  126.9
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2S,5R)-1-benzyl 2-ethyl 5-((4S,5S)-2,2-dimethyl-5-((S)-oxiran-2-yl)-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of a protected trihydroxyindolizidine 3-carboxylate via a hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to a d-ribose-derived exo-glycal

  摘要：

  A protected trihydroxyindolizidine 3-carboxylate was prepared by a 6-endo epoxide cleavage, which in turn was intermediately formed from the hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.12.022
• 作为产物：
  描述：

  (2S,5R)-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-2-carboxylate 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of a protected trihydroxyindolizidine 3-carboxylate via a hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to a d-ribose-derived exo-glycal

  摘要：

  A protected trihydroxyindolizidine 3-carboxylate was prepared by a 6-endo epoxide cleavage, which in turn was intermediately formed from the hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.12.022