Back to Search
Start Over
Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones.
- Source :
-
Sustainable Chemistry . Sep2022, Vol. 3 Issue 3, p300-311. 12p. - Publication Year :
- 2022
-
Abstract
- Sugar amides, such as aldonamides, are interesting, sugar-based molecules used in various fields, from detergency to medicine. Nevertheless, their valorization, especially as alternatives to petroleum-based substances, can be slowed down by their synthetic pathway, which is generally not in accordance with green chemistry principles, and is also not economically competitive. We propose herein a fast procedure for the synthesis of aldonamide-derived glycoconjugates with mechanochemistry. The conditions were first optimized with galactonolactone, used as a model lactone, and dodecylamine. After only 5 min of grinding of stoechiometric amounts of amine and lactone, in the presence of water used as a Liquid Assisted Grinding (LAG) agent, the corresponding galactonamide was isolated with a high yield (90%) after a simple aqueous work-up. The optimized conditions were then applied to a wide variety of amines and sugar lactones, showing the versatility of the methodology. Gluco- and ribono-lactone exhibited similarly excellent reactivity, showing that the procedure is not sugar-dependent. Furthermore, the procedure was shown to be compatible with various functional groups such as alkene, alkyne, thiol, ester and hydroxyl. [ABSTRACT FROM AUTHOR]
- Subjects :
- *LACTONES
*SUGAR
*GLYCOCONJUGATES
*SUSTAINABLE chemistry
*AMIDES
Subjects
Details
- Language :
- English
- ISSN :
- 26734079
- Volume :
- 3
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Sustainable Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 159350995
- Full Text :
- https://doi.org/10.3390/suschem3030019