1. Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks
- Author
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Shazia Anjum, Joseph E. Rubin, Natasha D. Vetter, and David R. J. Palmer
- Subjects
chemistry.chemical_classification ,congenital, hereditary, and neonatal diseases and abnormalities ,Stereochemistry ,Organic Chemistry ,Glycoside ,Biochemistry ,chemistry.chemical_compound ,Chromatographic separation ,chemistry ,Drug Discovery ,Electronic effect ,Stereoselectivity ,Glycosyl ,Acyl group - Abstract
Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1′-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di- O -isopropylidene-α- d -glucofuranose. The key α,β-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O -2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1′-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak anti-staphylococcal activity.
- Published
- 2013
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