D,L-threo-2-hydroxy-3-(p-toluenesulfonamido)-3-phenylpropionic acid

• 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: D,L-threo-2-hydroxy-3-(p-toluenesulfonamido)-3-phenylpropionic acid
• 英文别名: (2R,3S)-2-hydroxy-3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoic acid
• 化学式: C₁₆H₁₇NO₅S
• 分子量: 335.381
• InChiKey: GMKXVSUIANQGOT-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D,L-threo-2-hydroxy-3-(p-toluenesulfonamido)-3-phenylpropionic acid 在 ruthenium trichloride 过碘酸 作用下， 生成 (2S)-2-phenyl-2-(tosylamino)acetic acid
  参考文献：
  名称：

  Novel Asymmetric C−C Bond Formation Process Promoted by Et₂AlCl and Its Application to the Stereoselective Synthesis of Unusual β-Branched Baylis−Hillman Adducts

  摘要：

  DOI：

  10.1021/jo981976l
• 作为产物：
  描述：

  (2S,3R)-2-hydroxy-N,N-dimethyl-3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanamide 在 盐酸 作用下， 以93%的产率得到D,L-threo-2-hydroxy-3-(p-toluenesulfonamido)-3-phenylpropionic acid
  参考文献：
  名称：

  A Highly Efficient Aminohydroxylation Process

  摘要：

  DOI：

  10.1002/anie.199726371

文献信息

• Aminohydroxylation of Olefins
  申请人：The Scripps Research Institute

  公开号：US06350905B1

  公开（公告）日：2002-02-26

  Osmium-catalyzed aminohydroxylation reactions are accelerated and expanded in scope by the use of olefinic substrates having ionic groups, either anionic or cationic. The use of ionic groups on olefinic substrates also extends the aminohydroxylatable positions of unsaturations to include &agr;,&bgr;, &bgr;,&ggr;, and &ggr;,&dgr; positions, with respect to such ionic groups. A mechanism for the disclosed acceleration and extension is provided.

  铂催化的氨羟基化反应通过使用具有离子基团的烯烃底物（无论是阴离子还是阳离子）而得到加速和扩展。在烯烃底物上使用离子基团还将氨羟基化位置扩展到与这些离子基团相关的α，β，β，γ和γ，δ位置。提供了所述加速和扩展的机制。
• A Practical and Highly Efficient Aminohydroxylation of Unsaturated Carboxylic Acids
  作者：Valery V. Fokin、K. Barry Sharpless

  DOI：10.1002/1521-3773(20010917)40:18<3455::aid-anie3455>3.0.co;2-i

  日期：2001.9.17
• [EN] SYNTHESIS OF alpha , beta -SUBSTITUTED AMINO AMIDES, ESTERS AND ACIDS<br/>[FR] SYNTHESE D'AMIDES, ESTERS ET ACIDES AMINES alpha , beta -SUBSTITUES
  申请人：——

  公开号：WO1998042657A1

  公开（公告）日：1998-10-01

  [EN] alpha , beta -Unsaturated amides and esters are converted to alpha , beta -substituted amino amides, esters, and acids. An alpha , beta -unsaturated amide or ester is first converted to an alpha , beta hydroxysulfonamide or hydroxycarbamate amide or ester using an osmium-catalyzed aminohydroxylation. The alpha , beta -hydroxysulfonamide or hydroxycarbamate amides or esters is then cyclodehydrated to produce a alpha , beta -N-sulfonyl- or the alpha , beta -N-carbamoylaziridine amide or ester. The ring of aziridine intermediate is then nucleophilically opened in a regioselective manner with a variety of nucleophiles to give the DOLLAR g(a, beta -substituted amino- amides or esters. Preferred nucleophiles include sulfur, oxygen, carbon, and nitrogen nucleophiles.
  [FR] Des amides et esters alpha , beta -insaturés sont convertis en amides, esters et acides aminés alpha , beta -substitués. On commence par convertir un amide ou un ester alpha , beta -insaturé en alpha , beta -hydroxysulfonamide ou hydroxycarbamate amide ou ester en utilisant une aminohydroxylation catalysée à l'osmium. On procède ensuite à la cyclodéshydratation du alpha , beta -hydroxysulfonamide ou hydroxycarbamate amide ou ester de façon à donner un alpha , beta -N-)sulfonyl- ou le alpha , beta -N-)carbamoylaziridine amide ou ester. Ce cycle d'intermédiaire aziridine est alors nucléophiliquement ouvert de façon régiosélective, une grande diversité de nucléophiles venant donner les amides ou esters aminés alpha , beta -substitués. Les nucléophiles préférés sont ceux du soufre, de l'oxygène, du carbone et de l'azote.
  [EN] alpha , beta -Unsaturated amides and esters are converted to alpha , beta -substituted amino amides, esters, and acids. An alpha , beta -unsaturated amide or ester is first converted to an alpha , beta hydroxysulfonamide or hydroxycarbamate amide or ester using an osmium-catalyzed aminohydroxylation. The alpha , beta -hydroxysulfonamide or hydroxycarbamate amides or esters is then cyclodehydrated to produce a alpha , beta -N-sulfonyl- or the alpha , beta -N-carbamoylaziridine amide or ester. The ring of aziridine intermediate is then nucleophilically opened in a regioselective manner with a variety of nucleophiles to give the DOLLAR g(a, beta -substituted amino- amides or esters. Preferred nucleophiles include sulfur, oxygen, carbon, and nitrogen nucleophiles.
• Novel Asymmetric C−C Bond Formation Process Promoted by Et₂AlCl and Its Application to the Stereoselective Synthesis of Unusual β-Branched Baylis−Hillman Adducts
  作者：Guigen Li、Han-Xun Wei、Bruce R. Whittlesey、Nassim N. Batrice

  DOI：10.1021/jo981976l

  日期：1999.2.1
• A Highly Efficient Aminohydroxylation Process
  作者：A. Erik Rubin、K. Barry Sharpless

  DOI：10.1002/anie.199726371

  日期：1997.12.15