tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(benzo[d][1,3]dioxol-6-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate | 927683-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(benzo[d][1,3]dioxol-6-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[(1R)-1-(1,3-benzodioxol-5-yl)-3-methoxy-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 927683-13-4
• 化学式: C₂₁H₂₉NO₇
• 分子量: 407.464
• InChiKey: AERMAOSPIMELBP-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(benzo[d][1,3]dioxol-6-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (4R,5R)-1-acetyl-4-(benzo[d][1,3]dioxol-6-yl)-5-(hydroxymethyl)pyrrolidin-2-one
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029
• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 、 tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 magnesium 、 copper(l) iodide 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以92%的产率得到tert-butyl (R)-4-((R)-2-(methoxycarbonyl)-1-(benzo[d][1,3]dioxol-6-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029

文献信息

• A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates
  作者：Shiva K. Rastogi、Alexander Kornienko

  DOI：10.1016/j.tetasy.2006.11.029

  日期：2006.11

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.