(R)-phenylglycine benzyl ester p-toluenesulfonate | 133545-89-8

• 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: (R)-phenylglycine benzyl ester p-toluenesulfonate
• 英文别名: [(1R)-2-(benzyloxy)-2-oxo-1-phenylethyl]ammonium 4-methyl-1-benzensulfonate；(R)-2-phenylglycine benzyl ester p-toluene sulfonic acid salt；D-Phenylglycine benzyl ester p-toluenesulfonate；benzyl phenylglycinate tosylate
• CAS: 133545-89-8
• 化学式: C₇H₈O₃S*C₁₅H₁₅NO₂
• 分子量: 413.494
• InChiKey: NUKYSRPSEVRDQK-PFEQFJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  106.69
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-phenylglycine benzyl ester p-toluenesulfonate 在 钯 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Salts of N,N′-Oxalylbis(phenylglycine)s and 1-Phenylethylamines: Structural Variation of Layered Materials Induced by Stereochemistry

  摘要：

  Salts between (R,R)- or meso-N,N'-oxalylbis(phenylglycine) 1 and (R)-, (S)-, or (+/-)-1-phenylethylamine 2 construct three different layer structures depending on their stereochemistry. By X-ray crystallography, it is elucidated that the formation of a hydrogen bonding network between the amino and carboxyl groups and the planarity of the oxalyl functionality are important to construct the sheet structure. The salt of (R,R)-1 and 2 forms a bilayer or puckered structure, whereas the salt of meso-1 and 2 constructs a monolayer structure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01059-5
• 作为产物：
  描述：

  D-苯甘氨酸甲酯盐酸盐 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (R)-phenylglycine benzyl ester p-toluenesulfonate
  参考文献：
  名称：

  Oxygen Alkylation of Schiff Base Derivatives of Amino Acids

  摘要：

  氨基酸和二肽的高亚胺酯1a-h和7a-b通过皂化苯甲酮席夫碱甲酯3a-d和6，采用相转移技术，随后与烷基卤进行O-烷基化，产率在68-91%之间。该过程在α-碳上保留构型，除了苯基甘氨酸衍生物外。

  DOI：

  10.1055/s-1991-26625

文献信息

• One-step preparation of enantiopure l- or d-amino acid benzyl esters avoiding the use of banned solvents
  作者：Cristiano Bolchi、Francesco Bavo、Marco Pallavicini

  DOI：10.1007/s00726-017-2400-y

  日期：2017.5

  phenylglycine, tyrosine and methionine, are formed enantiomerically pure under these new reaction conditions thus validating the solvents replacement. Contrariwise, toluene cannot be used in place of benzene or carbon tetrachloride because leading to partially or totally racemized amino acid benzyl esters depending on the polar effect of the amino acid α-side chain as expressed by Taft’s substituent constant

  氨基酸苄基酯的对映体是非常重要的合成中间体。目前，它们中的许多是通过在回流的苯或四氯化碳中用苯甲醇和对甲苯磺酸处理，共沸除去水，然后通过加入乙醚而以甲苯磺酸盐的形式沉淀而制备的。在这里，我们报告了一个非常有效的准备八个l-或d-氨基酸苄基酯（Ala，Phe，Tyr，Phg，Val，Leu，Lys，Ser），其中使用环己烷作为水共沸溶剂和乙酸乙酯除去这些高度危险的溶剂，以沉淀甲苯磺酸盐。经过一些后处理的改进和较低的收率，该方法也可用于蛋氨酸。手性HPLC分析表明，在这些新的反应条件下，所有苄基酯，包括高度可消旋的苄基酯，如苯基甘氨酸，酪氨酸和蛋氨酸的对映体，都是对映体纯的，从而验证了溶剂的替代性。相反，不能使用甲苯代替苯或四氯化碳，因为它会导致部分或全部外消旋的氨基酸苄酯，这取决于塔夫脱取代基常数（σ*）表示的氨基酸α-侧链的极性作用。
• WO2006/86562
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of a library of chiral α-amino acid-based borate counteranions and their application to copper catalyzed olefin cyclopropanation
  作者：David B. Llewellyn、Bruce A. Arndtsen

  DOI：10.1016/j.tetasy.2005.04.004

  日期：2005.5

  Twenty borate counteranions have been prepared from tartaric acid and alpha-amino acid derivatives. Ion pairing of these anions to a copper cation can be Used to induce enantioselectivity into the copper catalyzed cyclopropanation of styrene. Structural modification of the anion provides insight into the importance of each component of the counteranion in asymmetric induction. (C) 2005 Published by Elsevier Ltd.
• Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (<i>R</i>)-Phenylglycyl-(<i>R</i>)-phenylglycine and the Crystal Structures of the Inclusion Cavities
  作者：Motohiro Akazome、Yuki Ueno、Haruko Ooiso、Katsuyuki Ogura

  DOI：10.1021/jo991051l

  日期：2000.1.1

  Crystalline (R)-phenylglycyl-(R)-phenylglycine [(R,R)-1] includes methyl phenyl sulfoxides (2 and 3) and benzyl methyl sulfoxides (4) with high enantioselectivity. The dipeptide exhibited different stereoselectivity depending on four structural isomers of methyl tolyl sulfoxide (C8H10OS): R for methyl 2-tolyl sulfoxide, S for methyl 3-tolyl sulfoxide, and racemic for methyl 4-tolyl sulfoxide. A structural isomer, benzyl methyl sulfoxide, was included in racemic form. Chlorophenyl methyl sulfoxides 3 (C7H7ClOS) with a similar volume showed the same enantioselectivity for their recognition. By single-crystal X-ray analyses of these inclusion compounds, it was elucidated that (R,R)-1 molecules self-assembled to form layer structures and included the sulfoxides between these layers and that the origin of the enantioselectivity based on chiral cavities was induced by conformation of the C-terminal phenyl group of the dipeptide. The relative position between the ammonio proton and the C-terminal phenyl group in one molecule of the dipeptide determined the stereochemistry of the methyl sulfinyl groups to be recognized. Various positional isomers of methyl xylyl sulfoxide having the formula of C9H12OS were subjected to the enantioselective inclusion by (R,R)-1 crystals and these results are also discussed.
• Sheet Structure of an <scp>l</scp>,<scp>d</scp>-Dipeptide Aggregate:  Inclusion Compounds of (<i>S</i>)-Phenylglycyl-(<i>R</i>)-phenylglycine with Amides
  作者：Motohiro Akazome、Kyoko Senda、Katsuyuki Ogura

  DOI：10.1021/jo0204451

  日期：2002.12.1

  A simple dipeptide, (S)-phenylglycyl-(R)-phenylglycine (S,R-1), formed inclusion compounds with a small amide such as formamide, acetamide, N,N-dimethylformamide (DMF), or N,N-dimethylacetamide. By single-crystal X-ray analysis, the inclusion compounds were shown to have a wavy layer structure. The molecules of S,R-1 are arranged in parallel via ionic pairing of the carboxyl and amino groups to construct the wavy layers. The guest molecules were accommodated in a, channel cavity between the layers by means of hydrogen bonding with +NH3 Of S,R-1. The cavity, is surrounded by the phenyl groups of S,R-1 that conformationally rotate so as to make the cavity size fit the guest amide.