AI Article Synopsis
- - A new method has been developed to create pure β-S-glycopyranosides, a type of carbohydrate compound, using peracetate donors in the presence of InBr3 and chloroform.
- - The process involves deacylating the intermediates under specific conditions known as Zemplén conditions.
- - The study tested five different monosaccharides and disaccharides as donors and five types of thiols as acceptors, providing extensive data on the characteristics of the resulting compounds via techniques like NMR and mass spectrometry.
Article Abstract
Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data ((1)H and (13)C, including COSY, HSQC and HMBC) are reported for compounds not previously described.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8876251 | PMC |
| http://dx.doi.org/10.1016/j.carres.2015.12.008 | DOI Listing |
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