methyl (2S,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]threoninate | 189291-08-5

• 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 (2S,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]threoninate
• 英文别名: methyl (2S,3R)-3-hydroxy-2-[(2,4,6-trimethylphenyl)sulfonylamino]butanoate
• CAS: 189291-08-5
• 化学式: C₁₄H₂₁NO₅S
• 分子量: 315.39
• InChiKey: RBUODSDHSPWVGA-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]threoninate 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)-2,4,6-trimethylbenzenesulfonamide
  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：

  2,4,6-三甲基苯磺酰氯 、 L-苏氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到methyl (2S,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]threoninate
  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

文献信息

• Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group:  A Thermodynamic Preference for Chiral Alkyl (2<i>E</i>)-4,5-<i>cis</i>-4,5-Epimino-<i>N</i>-(alkyl- or arylsulfonyl) 2-Enoates over the Other Three Stereoisomers
  作者：Toshiro Ibuka、Norio Mimura、Hiroaki Ohno、Kazuo Nakai、Masako Akaji、Hiromu Habashita、Hirokazu Tamamura、Yoshihisa Miwa、Tooru Taga、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1021/jo962094u

  日期：1997.5.1

  Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal that 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthesis of (E)-alkene dipeptide isosteres having the desired stereochemistries from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl)

  钯（0）催化的五组四个四个立体异构体4,5-表氨-N-（甲磺酰基）或-N-（芳基磺酰基）2-烯酸酯的反应表明，4,5-顺式（（2E））异构体的热力学性质更高根据计算，该化合物比其他异构体稳定。还提出了由不想要的立体异构体4，5-表观氨基-N-（芳基磺酰基）2-烯酸酯的具有所需立体化学的（E）-烯烃二肽等排物的高度立体选择性合成。
• <scp>l</scp>-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction
  作者：Fangrui Zhong、Youqing Wang、Xiaoyu Han、Kuo-Wei Huang、Yixin Lu

  DOI：10.1021/ol103145g

  日期：2011.3.18

  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.