Spiro[2.3]hexane‐ and Spiro[3.3]heptane‐derived α‐Amino Acids: Synthesis and Isoelectric Point Evaluation,ChemistrySelect

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Spiro[2.3]hexane‐ and Spiro[3.3]heptane‐derived α‐Amino Acids: Synthesis and Isoelectric Point Evaluation
ChemistrySelect ( IF 1.9 ) Pub Date : 2024-08-14 , DOI: 10.1002/slct.202402108
Andrii Malashchuk _{1,

2} , Anton V. Chernykh _{1,

3} , Oleksandr S. Liashuk _{1,

2} , Rustam Hurbanov ₁ , Mykhailo Lomaka ₁ , Hennadii Tkachuk ₁ , Dmitry Granat ₁ , Oleksandr O. Grygorenko _{1,

2}

Affiliation

An efficient synthesis of spiro[2.3]hexane‐ and spiro[3.3]heptane‐derived α‐amino acids is reported. The used methods are divided on two different approaches. First of them involves modification of commercially available spirocyclic diesters via monohydrolysis, Curtius rearrangement and functional groups deprotection sequence. Alternative approach was based on Bucherer ‐ Bergs hydantoine synthesis with its subsequent cleavage to the target amino acid fragment. The proposed synthetic schemes offer the desired product in 31–52 % overall yield on up to 22.5 g scale. Acid‐base titration of the obtained spirocyclic amino acids revealed lowered pI values compared to the parent 1‐amino‐cyclohexane‐ and ‐cycloheptanecarboxylic acids.

中文翻译：

螺[2.3]己烷和螺[3.3]庚烷衍生的α-氨基酸：合成和等电点评估

据报道，螺[2.3]己烷和螺[3.3]庚烷衍生的α-氨基酸的有效合成。使用的方法分为两种不同的方法。首先涉及对市售螺环二酯的改性通过单水解、Curtius 重排和官能团脱保护序列。替代方法基于 Bucherer-Bergs 乙内酰脲合成，随后裂解为目标氨基酸片段。所提出的合成方案以 31-52% 的总产率提供所需的产品，规模高达 22.5 g。所得螺环氨基酸的酸碱滴定显示 p 降低我与母体1-氨基-环己烷-和-环庚烷甲酸相比的值。

更新日期：2024-08-14

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