Abstract

A short and scalable process for the preparation of multi-gram quantities of orthogonally protected bis(aminomethyl)malonic acid in good yield from readily available starting material is described. These orthogonally protected amino acids are important building blocks to make peptides based drugs, glycoconjugates, and in the total synthesis of peptide natural products. The newly developed route has only six steps with an overall yield of 27%, which involves nucleophilic attack of a malonate on an imide as one of the key steps.

A short and scalable process for the preparation of multi-gram quantities of orthogonally protected bis(aminomethyl)malonic acid in good yield from readily available starting material is described. These orthogonally protected amino acids are important building blocks to make peptides based drugs, glycoconjugates, and in the total synthesis of peptide natural products. The newly developed route has only six steps with an overall yield of 27%, which involves nucleophilic attack of a malonate on an imide as one of the key steps.

中文翻译：

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正交保护的双（氨基甲基）丙二酸的短而可扩展的合成：获得生物活性大环肽。

摘要

描述了一种短程且可扩展的方法，该方法用于从容易获得的起始原料中以高收率制备数克量的正交保护的双（氨基甲基）丙二酸。这些正交保护的氨基酸是制造基于肽的药物，糖结合物以及在肽天然产物的总合成中的重要组成部分。新开发的路线只有六个步骤，总产率为27％，这是关键步骤之一，其中丙二酸对酰亚胺的亲核攻击。

描述了一种短程且可扩展的方法，该方法用于从容易获得的起始原料中以高收率制备数克量的正交保护的双（氨基甲基）丙二酸。这些正交保护的氨基酸是制造基于肽的药物，糖结合物以及在肽天然产物的总合成中的重要组成部分。新开发的路线只有六个步骤，总产率为27％，这是关键步骤之一，其中丙二酸对酰亚胺的亲核攻击。