Crich David, Sasaki Kaname, Rahaman Md Yeajur, Bowers Albert A
Centre de Recherche CNRS de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
J Org Chem. 2009 May 15;74(10):3886-93. doi: 10.1021/jo900532e.
Opening cyclic monothioanhydrides by amines provides a convenient entry into amido thioacids that can be trapped in situ by 2,4-dinitrobenzenesulfonamides, by electron-deficient azides, or by amines in the presence of Sanger's reagent leading, in each case, to dissymmetric diamides in what can be considered a one-pot, three-component coupling sequence. The use of monothiomaleic anhydride and bifunctional nucleophiles such as amino thiols provides access to heterocyclic amides. The low reactivity of cyclic monothioanhydrides toward alcohols enables the use of methanol as solvent and obviates the need for the protection of alcohols in the various reaction components. Reaction of N-benzyloxycarbonyl-l-aspartic monothioanhydride with unprotected glycosyl amines, followed by capture of the thioacid intermediate with N-sulfonyl amino acid derivatives results in a three-component convergent synthesis of glycosylated peptides.
胺类物质开环环化单硫代酸酐可方便地制得酰胺基硫代酸，该产物能在原位被2,4-二硝基苯磺酰胺、缺电子叠氮化物或在桑格试剂存在下的胺类物质捕获，在每种情况下，均可通过一锅法三组分偶联反应得到不对称二酰胺。使用单硫代马来酸酐和双官能亲核试剂（如氨基硫醇）可制得杂环酰胺。环化单硫代酸酐对醇类物质的低反应活性使得甲醇可作为溶剂使用，避免了对各种反应组分中的醇进行保护的需要。N-苄氧羰基-L-天冬氨酸单硫代酸酐与未保护的糖基胺反应，随后用N-磺酰基氨基酸衍生物捕获硫代酸中间体，可实现糖基化肽的三组分汇聚合成。
