(2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-[(S)-(4-methylphenylsulfinamido)]-5-benzyloxypentanamide | 1287731-62-7

• 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: (2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-[(S)-(4-methylphenylsulfinamido)]-5-benzyloxypentanamide
• 英文别名: (2S,3S)-N-methoxy-N,2-dimethyl-3-[[(S)-(4-methylphenyl)sulfinyl]amino]-5-phenylmethoxypentanamide
• CAS: 1287731-62-7
• 化学式: C₂₂H₃₀N₂O₄S
• 分子量: 418.557
• InChiKey: JLNQSVQRQJNTBN-LJNDWVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 (2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-[(S)-(4-methylphenylsulfinamido)]-5-benzyloxypentanamide 以 四氢呋喃 为溶剂， 以40%的产率得到N-[(3S,4S)-(+)-1-(benzyloxy)-4-methyl-5-oxononan-3-yl]-4-methylbenzenesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352
• 作为产物：
  描述：

  (S)-(+)-对甲基苯亚磺酰胺 在 titanium(IV) tetraethanolate 、 正丁基锂 、 sodium hexamethyldisilazane 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,3S)-(+)-N-methoxy-N,2-dimethyl-3-[(S)-(4-methylphenylsulfinamido)]-5-benzyloxypentanamide
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352

文献信息

• Asymmetric Synthesis of <i>anti</i>-α-Substituted β-Amino Ketones from Sulfinimines
  作者：Franklin A. Davis、Peng Xu

  DOI：10.1021/jo2002352

  日期：2011.5.6

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.