(2R,3R)-methyl 3-hydroxy-2-(naphthalene-2-sulfonamido)butanoate | 1310338-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3R)-methyl 3-hydroxy-2-(naphthalene-2-sulfonamido)butanoate
• CAS: 1310338-66-9
• 化学式: C₁₅H₁₇NO₅S
• 分子量: 323.37
• InChiKey: PZGOTSIVUKUTSR-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-methyl 3-hydroxy-2-(naphthalene-2-sulfonamido)butanoate 在 咪唑 、 甲醇 、 锂硼氢 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-((2R,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-hydroxybutan-2-yl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  l-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction

  摘要：

  A series of novel bifunctional phosphine sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. L-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities.

  DOI：

  10.1021/ol103145g
• 作为产物：
  描述：

  L-苏氨酸甲酯盐酸盐 、 2-萘磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(2R,3R)-methyl 3-hydroxy-2-(naphthalene-2-sulfonamido)butanoate
  参考文献：
  名称：

  l-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction

  摘要：

  A series of novel bifunctional phosphine sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. L-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities.

  DOI：

  10.1021/ol103145g