(S)-N^α-phthaloyl-O-benzyltyrosine chloride | 88036-14-0

• 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: (S)-N^α-phthaloyl-O-benzyltyrosine chloride
• 英文别名: N-phthaloyl-O-benzyl-L-tyrosyl chloride；N^α-Pht-Tyr(Bn)-Cl；(2S)-2-(1,3-dioxoisoindol-2-yl)-3-(4-phenylmethoxyphenyl)propanoyl chloride
• CAS: 88036-14-0
• 化学式: C₂₄H₁₈ClNO₄
• 分子量: 419.864
• InChiKey: VLQZAODDSSOAFJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-N^α-phthaloyl-O-benzyltyrosine chloride 在 sodium carbonate 、 对甲苯磺酸 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 17.0h， 生成 3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-benzyloxyphenyl)propanoyl]-1,3-oxazolidin-5-one
  参考文献：
  名称：

  Efficient Synthesis of (S)-4-Phthalimido-1,3,4,5- tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic Acid (Pht-Hba(2,6-Cl₂-Bn)-Gly-OH)¹

  摘要：

  4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl-2-Bn)-Gly-OH 17 starting from the commercially available tyro sine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl-2-Bn)-Gly-OH 15 is converted,to the 1,3-oxazolidin-5-one 16 Which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.

  DOI：

  10.1021/jo000530d
• 作为产物：
  描述：

  (S)-N^α-phthaloyl-O-benzyltyrosine 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 1.0h， 以93%的产率得到(S)-N^α-phthaloyl-O-benzyltyrosine chloride
  参考文献：
  名称：

  Replacement of the peptide-backbone amides connecting Tyr-Gly and Gly-Gly in leucine-enkephalin with ketomethylene groups: synthesis and biological activity

  摘要：

  A peptide analogue of Leu-enkephalin was synthesized in which the amide linkages between Tyr-Gly and Gly-Gly were replaced by ketomethylene groups. The resulting analogue, 12, had 1/4000th and 1/2400th the opiate receptor binding activity of Leu-enkephalin when (3H) [D-Ala2,D-Leu5]enkephalin and (3H)naloxone, respectively, were used as tritiated ligands. When tested for analgesia in mice by the tail-flick assay, 12 produced analgesia in 50% of the mice tested at a dose of 24.3 micrograms/mouse (icv), while the ED50 of Leu-enkephalin is 240 micrograms/mouse (icv). At a dose of 40 micrograms/mouse (icv) or higher, 12 caused convulsions in a dose-dependent manner. No analgesia was observed after intravenous (iv) administration of 240 micrograms/mouse of 12.

  DOI：

  10.1021/jm00368a003

文献信息

• Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates
  作者：Achille Barco、Simonetta Benetti、Paola Bergamini、Carmela De Risi、Paolo Marchetti、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1016/s0040-4039(99)01573-7

  日期：1999.10

  Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds.

  通过适当的酰氯和亚磷酸三乙酯之间的Arbuzov反应，以硼烷和恶唑硼烷为催化剂，还原β-邻苯二甲酰亚胺基-α-羟基膦酸酯，可提供高收率和高非对映选择性的β-邻苯二甲酰亚胺基-α-羟基膦酸酯。氨基的脱保护得到标题化合物。