Found 1 publication.
Displayed publication 1
Expand all publications
Collapse all publications
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. (Article ID: 3587)
Guo H, O'Doherty GA
De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
Journal of Organic Chemistry 73(14) (2008)
5211-5220
A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective acylation were employed for the assembly of the L-rhamno-trisaccharide building block. The anthrose building block also required a palladium-catalyzed azide allylation and a triflate inversion to set the gluco-stereochemistry in addition to Luche reduction and dihydroxylation
synthesis, tetrasaccharide, glycosylation, acylation, Bacillus anthracis, Stereoisomerism
NCBI PubMed ID: 18563936Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: george.odoherty
mail.wVu.edu
Institutions: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis
The publication contains the following compound(s):
- Compound ID: 7887
|
3HOiVl-(1-4)-b-D-Quip4N2Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-L-Rha
3HOiVl = 3-hydroxy-3-methylbutanoic acid |
Show graphically |
Structure type: oligomer
Trivial name: anthrax tetrasaccharide
Reference(s) to other database(s): GlycomeDB:
27777
Expand this publication
Collapse this publication
Total list of publication IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: <1 sec