A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including O-, methylene-, and fluoromethine-linked isosteres with diastereomeric ceramide segments and 2-amido substitutes.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5721664 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.6b02284 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.
Org Lett
September 2016
Hunter College, The City University of New York (CUNY), 695 Park Avenue, New York, New York 10021, United States.
A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including O-, methylene-, and fluoromethine-linked isosteres with diastereomeric ceramide segments and 2-amido substitutes.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!