methyl (4R)-4-[[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]amino]-6-hydroxyhexanoate | 1126897-29-7

• 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: methyl (4R)-4-[[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]amino]-6-hydroxyhexanoate
• CAS: 1126897-29-7
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: REZMJNVHPUMOLQ-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-碘乙醇 、 在 indium(III) chloride 、 羰基镁 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以33%的产率得到methyl (4R)-4-[[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]amino]-6-hydroxyhexanoate
  参考文献：
  名称：

  Synthesis of γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters

  摘要：

  Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.

  DOI：

  10.1021/ol802932v

文献信息

• Synthesis of γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters
  作者：Gregory K. Friestad、Koushik Banerjee

  DOI：10.1021/ol802932v

  日期：2009.3.5

  Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.