(S)-4-Benzyl-3-(2-triethylsilanyloxy-acetyl)-oxazolidin-2-one | 289618-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-4-Benzyl-3-(2-triethylsilanyloxy-acetyl)-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-(2-triethylsilyloxyacetyl)-1,3-oxazolidin-2-one
• CAS: 289618-96-8
• 化学式: C₁₈H₂₇NO₄Si
• 分子量: 349.502
• InChiKey: XFDOCLSOXBMVLX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 (S)-4-Benzyl-3-(2-triethylsilanyloxy-acetyl)-oxazolidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以73%的产率得到(S)-4-Benzyl-3-((R)-2-triethylsilanyloxy-pent-4-enoyl)-oxazolidin-2-one
  参考文献：
  名称：

  Diastereoselective Alkylations of Oxazolidinone Glycolates:  A Useful Extension of the Evans Asymmetric Alkylation

  摘要：

  [GRAPHICS]The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols, Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation, Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

  DOI：

  10.1021/ol006091m
• 作为产物：
  描述：

  (S)-(+)-4-苄基-3-苄氧基乙酰基-2-恶唑烷酮 在 palladium dihydroxide 咪唑 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-Benzyl-3-(2-triethylsilanyloxy-acetyl)-oxazolidin-2-one
  参考文献：
  名称：

  Diastereoselective Alkylations of Oxazolidinone Glycolates:  A Useful Extension of the Evans Asymmetric Alkylation

  摘要：

  [GRAPHICS]The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols, Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation, Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

  DOI：

  10.1021/ol006091m

文献信息

• Diastereoselective Alkylations of Oxazolidinone Glycolates:  A Useful Extension of the Evans Asymmetric Alkylation
  作者：Michael T. Crimmins、Kyle A. Emmitte、Jason D. Katz

  DOI：10.1021/ol006091m

  日期：2000.7.1

  [GRAPHICS]The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols, Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation, Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.