(R)-2-benzamido-3-iodopropanoic acid | 354526-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-benzamido-3-iodopropanoic acid
• 英文别名: (R)-(-)-2-(N-benzoyl-amino)-3-iodo propanoic acid；(R)-α-benzamido-β-iodo-propanoic acid；(2R)-2-benzamido-3-iodopropanoic acid
• CAS: 354526-83-3
• 化学式: C₁₀H₁₀INO₃
• 分子量: 319.099
• InChiKey: WCANNAKSBNZCRK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-benzamido-3-iodopropanoic acid 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  o-Boronato- and o-Trifluoroborato–Phosphonium Salts Supported by l-α-Amino Acid Side Chain

  摘要：

  The synthesis of o-boronato- and o-trifluoroborato-phosphonium salts supported by the L-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with) beta- or gamma-iodo amino acid derivatives which are prepared from L-serine or L-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato-phosphonium amino esters, respectively. The usefulness of these compounds in peptide coupling was demonstrated by coupling an o-boronato-phosphonium amino ester with an aspartic acid moiety. When the o-boronato-phosphonium amino acid or dipeptide derivatives were mixed with fluoride, the corresponding o-trifluoroborated products were cleanly and rapidly obtained in high isolated yields. The hydrolysis of these compounds at room temperature using a phosphate buffer pH 7/CD3CN mixture has shown only traces of free fluoride F- after several days. Finally, a preliminary radiolabeling essay has proven the facile [F-18]-fluoride incorporation and high stability of the radiolabeled product in aqueous conditions. Indeed, this new class of boron-phosphonium amino acid derivatives shows promising properties for their applications in synthesis and labeling of peptides.

  DOI：

  10.1021/acs.joc.5b00246
• 作为产物：
  描述：

  (S)-(+)-4,5-二氢-2-苯基-4-噁唑羧酸甲酯 在 sodium hydroxide 、 碘代三甲硅烷 作用下， 以 氯仿 、 水 为溶剂， 反应 51.0h， 生成 (R)-2-benzamido-3-iodopropanoic acid
  参考文献：
  名称：

  有效合成β-卤素保护的l-丙氨酸及其β-phosph衍生物

  摘要：

  由1-丝氨酸制备的恶唑啉与三甲基甲硅烷基卤化物（TMSX）的开环导致β-卤代-N-苯甲酰基-α-氨基酯的产率高至优异。β-溴或-碘氨基酯对三苯膦进行季铵化可得到相应的β-salts盐，总收率可达93％，ee≥96％。酯官能团的水解得到带有N-苯甲酰基-α-氨基酸取代基的phospho盐，具有部分消旋作用。但是，TMSX与羧酸盐的反应是通过将起始的恶唑啉酯皂化而制备的，提供了相应的β-卤代-N-苯甲酰基-α-氨基酸，产率为70-95％。三苯基膦被溴或碘衍生物季铵化导致ization盐具有游离酸功能，产率为95％，而没有外消旋作用。通过从恶唑啉开始的一锅法以极好的总收率制备这些phospho盐，证明了这种合成的效率。

  DOI：

  10.1016/s0957-4166(03)00484-1

文献信息

• Triphenylphosphonium salts bearing an l-alanyl substituent: short synthesis and enantiomeric analysis by NMR
  作者：Franck Meyer、Jacques Uziel、Anne Marie Papini、Sylvain Jugé

  DOI：10.1016/s0040-4039(01)00650-5

  日期：2001.6

  short, practical stereospecific synthesis of triphenylphosphonium salts bearing an l-(N-benzoyl)-alanyl substituent from l-serine is described. The key step is the ring opening of an oxazoline salt derived from serine with trimethylsilyl halide, giving β-bromo or β-iodo alanine, which were used for the quaternization of triphenylphosphine. The phosphonium salts were obtained in 80% overall yield from serine

  描述了由1-丝氨酸的短的，实用的立体定向合成具有1-（N-苯甲酰基）-丙氨酰基取代基的三苯基phosph盐的方法。关键步骤是将衍生自丝氨酸的恶唑啉盐与三甲基甲硅烷基卤化物开环，得到β-溴或β-碘丙氨酸，将其用于三苯基膦的季铵化。从丝氨酸以80％的总收率获得phospho盐，并且在金鸡纳生物碱存在下，通过31 P NMR容易地确定其对映体纯度。