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Anomeric reactivity-based one-pot oligosaccharide synthesis: a rapid route to oligosaccharide libraries
- Source :
- The Journal of organic chemistry. 65(8)
- Publication Year :
- 2000
-
Abstract
- The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing a' one-pot sequential approach. With the help of the anomeric reactivity values of thioglycosides, using a thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor and donor coupled with another fully protected thioglycoside, a di- or trisaccharide is selectively formed without self-condensation and subsequently reacted in situ with an anomerically inactive glycoside (mono- or disaccharide) to form a tri- or tetrasaccharide in high overall yield. The approach enables the rapid assembly of 33 linear or branched fully protected oligosaccharides using designed building blocks. These fully protected oligosaccharides have been partially or completely deprotected to create 29 more structures to further increase the diversity of the library.
- Subjects :
- chemistry.chemical_classification
Anomer
Magnetic Resonance Spectroscopy
Hydroxyl Radical
Organic Chemistry
Molecular Sequence Data
Disaccharide
Glycoside
Oligosaccharides
Nuclear magnetic resonance spectroscopy
Oligosaccharide
Combinatorial chemistry
Catalysis
chemistry.chemical_compound
chemistry
Carbohydrate Sequence
Thioglycosides
Tetrasaccharide
Reactivity (chemistry)
Trisaccharide
Subjects
Details
- ISSN :
- 00223263
- Volume :
- 65
- Issue :
- 8
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....5031975d526d45bc8fe4c7d77ad8de99