N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester | 309264-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester
• 英文别名: methyl (2R)-2-(3-phenylpropanoylamino)-3-tritylsulfanylpropanoate
• CAS: 309264-63-9
• 化学式: C₃₂H₃₁NO₃S
• 分子量: 509.669
• InChiKey: NIEXFNAIUDYHLL-LJAQVGFWSA-N

物化性质

• 沸点：
  675.3±55.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester 在 三氟甲磺酸酐 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以84%的产率得到(4R)-2-phenylethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  使用三氟甲烷磺酸六苯基氧二phosph的仿生合成噻唑啉。

  摘要：

  DOI：

  10.1002/anie.200390059
• 作为产物：
  描述：

  Fmoc-Cys(Trt)-OMe 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester
  参考文献：
  名称：

  Titanium(IV)-Mediated Tandem Deprotection−Cyclodehydration of Protected Cysteine N-Amides:  Biomimetic Syntheses of Thiazoline- and Thiazole-Containing Heterocycles

  摘要：

  [GRAPHICS]The scope and limitations of TiCl4-mediated Delta(2)-thiazoline synthesis via tandem deprotection-dehydrocyclization of trityl-protected cysteine N-amides is presented. While chemical yields are acceptable (53-96%), the stereochemical outcomes vary on the basis of structural considerations and reaction conditions (22-99% ee). Racemization at the C(2)-exomethine position limits the utility of this method for the formation of a thiazoline within a peptide. Treatment of a tritylated Cys-Cys dipeptide with TiCl4 afforded the corresponding thiazole-thiazoline heterocycle 12 (38% yield, 97% ee).

  DOI：

  10.1021/ol000178q

文献信息

• [EN] 3-HYDROXY-4-OXO-1,2,3-TRIAZINES AND DERIVATIVES THEREOF FOR AMIDE AND ESTER BOND FORMATION<br/>[FR] 3-HYDROXY-4-OXO-1,2,3-TRIAZINES ET LEURS DERIVES POUR LA FORMATION DE LIAISONS AMIDE ET ESTER
  申请人：FRUTAROM LTD

  公开号：WO2005007634A1

  公开（公告）日：2005-01-27

  The present invention relates to the use of a compound of formula I as a coupling reagent in forming amide or ester bonds from a reaction between a carboxylic acid and an amine or an alcohol, respectively. The compounds of formula I are especially useful as coupling reagents in the preparation of peptide bonds during peptide synthesis. In particular, the compounds of formula I are useful in promoting the formation of reactive reaction intermediates, inhibiting side reactions and in suppression of racemization. In addition, the present invention provides novel compounds of Formula I, and salts of N-oxides thereof.

  本发明涉及在羧酸与胺或醇之间的反应中，将式I化合物用作偶联试剂形成酰胺或酯键。式I化合物在肽合成过程中特别有用作为偶联试剂。具体来说，式I化合物有助于促进反应中间体的形成，抑制副反应和消除旋光异构化。此外，本发明提供了式I的新化合物及其N-氧化物盐。
• Titanium(IV)-Mediated Tandem Deprotection−Cyclodehydration of Protected Cysteine <i>N</i>-Amides:  Biomimetic Syntheses of Thiazoline- and Thiazole-Containing Heterocycles
  作者：Prakash Raman、Hossein Razavi、Jeffery W. Kelly

  DOI：10.1021/ol000178q

  日期：2000.10.1

  [GRAPHICS]The scope and limitations of TiCl4-mediated Delta(2)-thiazoline synthesis via tandem deprotection-dehydrocyclization of trityl-protected cysteine N-amides is presented. While chemical yields are acceptable (53-96%), the stereochemical outcomes vary on the basis of structural considerations and reaction conditions (22-99% ee). Racemization at the C(2)-exomethine position limits the utility of this method for the formation of a thiazoline within a peptide. Treatment of a tritylated Cys-Cys dipeptide with TiCl4 afforded the corresponding thiazole-thiazoline heterocycle 12 (38% yield, 97% ee).
• A Biomimetic Synthesis of Thiazolines Using Hexaphenyloxodiphosphonium Trifluoromethanesulfonate
  作者：Shu-Li You、Hossein Razavi、Jeffery W. Kelly

  DOI：10.1002/anie.200390059

  日期：2003.1.3