methyl (+/-)-threo-N-acetyl-β-phenylserinate

• 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 (+/-)-threo-N-acetyl-β-phenylserinate
• 英文别名: Methyl (2R^*,3S^*)-2-(acetylamino)-3-hydroxy-3-phenylpropanoate；(2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid methyl ester；(2RS,3SR)-2-Acetylamino-3-hydroxy-3-phenyl-propionsaeure-methylester；methyl (2S,3R)-2-acetamido-3-hydroxy-3-phenylpropanoate
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: CLMZAZUSZFURFR-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (+/-)-threo-N-acetyl-β-phenylserinate 在 1,4-二氧六环 、 sodium hydroxide 、 氯化亚砜 、 氯仿 作用下， 生成 N-acetamido cinnamic acid
  参考文献：
  名称：

  Holland et al., Journal of the Chemical Society, 1953, p. 273,276

  摘要：

  DOI：
• 作为产物：
  描述：

  (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 在 sodium hydroxide 作用下， 生成 methyl (+/-)-threo-N-acetyl-β-phenylserinate
  参考文献：
  名称：

  Some Derivatives of the Stereoisomeric β-Phenylserines. Conversion of the Threo to the Erythro Form

  摘要：

  DOI：

  10.1021/jo50011a022

文献信息

• Synthesis of functionalized phenylalanine derivatives by ring opening reactions of 3-arylaziridine-2-carboxylic esters
  作者：Johan Legters、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/recl.19921110102

  日期：——

  respectively, due to the electron-releasing properties of the p-methoxy group. Only C3 attack was observed. Under the same conditions, 1b and 1c gave a clean SN2-type ring opening, leading to diastereomerically pure products 4b, 4c, 6b and 6c. Reaction of 1b with acetic acid gave 7 in an SN2-type ring opening at C3, followed by an ON acyl shift. Treatment of enantiopure (+ )-(2S,3R)-1b with benzenethiol

  描述了3-芳基氮丙啶-2-羧酸酯与各种亲核试剂的开环反应。选择外消旋的3-（4-甲氧基苯基）-，3-苯基-和3-（4-硝基苯基）氮丙啶-2-羧酸甲酯（分别为1a，1b和1c）作为底物。在不存在酸的情况下，没有开环发生。用乙醚氯化氢处理时，1a给出非对映异构体2a的混合物，而1b和1c分别给出区域异构体2b / 3b和2c / 3c的混合物。三氟化硼醚化物催化的1a反应由于对甲氧基的电子释放特性，用苯硫醇和吲哚与苯并噻吩还分别形成非对映体开环产物4a和6a。仅观察到C3攻击。在相同条件下，1b和1c产生干净的S N 2型开环，得到非对映异构纯产物4b，4c，6b和6c。1b与乙酸反应，在C3处的S N 2型开环中得到7 ，然后酰基转移为ON。对映体（+）-（2S，3R）-1b的治疗用苯硫醇，吲哚和乙酸与苯甲酸反应，得到相应的对映体纯的β-官能化的α-氨基酸衍生物。的官能1b中在氮气强烈增加的反应性：N-
• Peptide inhibitors of CDK2-cyclin A that target the cyclin recruitment-Site: structural variants of the C-Terminal Phe
  作者：Gail E Atkinson、Angela Cowan、Campbell McInnes、Daniella I Zheleva、Peter M Fischer、Weng C Chan

  DOI：10.1016/s0960-894x(02)00508-5

  日期：2002.9

  A focused series of octapeptides based on the lead compound H-His-Ala-Lys-Arg-Arg-Leu-Ile-Phe-NH2 1, in which the C-terminal phenylalanine residue was replaced by alpha and/or beta-modified variants, was synthesized using solid-phase chemistry. Both the L-threo-beta-hydroxy-phenylalanine (beta-phenylserine, Pse) and (2S)-phenylalaninol derivatives, as competitive binders at the cyclin-recruitment site, displayed potent inhibitory activity towards the CDK2-cyclin A complex. Unexpectedly, the D-threo-Pse derivatives also showed inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide
  作者：Hitoshi Tone、Marie Buchotte、Céline Mordant、Eric Guittet、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1021/ol900184d

  日期：2009.5.7

  The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of alpha-substituted, beta-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the L-serine residue and the natural product required a revision of the proposed structure.
• Chenevert, Robert; Letourneau, Martin; Thiboutot, Sonia, Canadian Journal of Chemistry, 1990, vol. 68, # 6, p. 960 - 963
  作者：Chenevert, Robert、Letourneau, Martin、Thiboutot, Sonia

  DOI：——

  日期：——
• Some Derivatives of the Stereoisomeric β-Phenylserines. Conversion of the Threo to the Erythro Form
  作者：William S. Fones

  DOI：10.1021/jo50011a022

  日期：1952.11