Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages Journal Article
| Authors: | Li, X.; Danishefsky, S. J. |
| Article Title: | Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages |
| Abstract: | This protocol describes the preparation of an N-methyl-asparagine-linked glycosyl amino acid, on the basis of a reaction between carboxylic acids and isonitriles. Under microwave/thermolysis, carboxylic acids can couple with isonitriles without an external catalyst to form N-formyl-amides, which may be further advanced to the corresponding amides, N-methyl amide and N-methyloyl amide. The example reaction of beta-galactopyranosyl isonitrile (7) with a protected aspartic acid under microwave condition in 30 min stereoselectively leads to a beta-galactopyranosyl-N-formyl-asparagine (9). Further chemical transformations readily convert 9 into beta-galactopyranosyl-N-methyl-asparagine (11). |
| Keywords: | chemistry; hydrogen bond; hydrogen bonding; chemical structure; molecular structure; nitriles; nitrile; carboxylic acids; amides; amide; carboxylic acid |
| Journal Title: | Nature Protocols |
| Volume: | 3 |
| Issue: | 10 |
| ISSN: | 1754-2189 |
| Publisher: | Nature Publishing Group |
| Date Published: | 2008-01-01 |
| Start Page: | 1666 |
| End Page: | 1670 |
| Language: | English |
| DOI: | 10.1038/nprot.2008.153 |
| PUBMED: | 18833204 |
| PROVIDER: | scopus |
| PMCID: | PMC2587016 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 6" - "Export Date: 17 November 2011" - "Source: Scopus" |
