Abstract
A straightforward synthetic strategy was developed for the synthesis of the tetrasaccharide repeating unit corresponding to the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71T in a very good yield adopting sequential glycosylation followed by removal of the p-methoxybenzyl (PMB) group in the same pot. Further, the synthetic strategy was modified by carrying out three stereoselective iterative glycosylations followed by in situ removal of the PMB group in one pot. The stereochemical outcome of the newly formed glycosidic linkages was excellent using thioglycoside derivatives as glycosyl donors and a combination of N-iodosuccinimide (NIS) and perchloric acid supported on silica (HClO4-SiO2) as the glycosyl activator.
Highlights
The development of plant-growth-promoting agents has become an attractive area of research in the agricultural sciences to reduce the need for chemical fertilizers, which cause environmental pollution, resistance in plant pathogens as well as high production costs of crops [1,2,3]
The retrosynthetic analysis suggested that a sequential glycosylation reaction using judiciously protected monosaccharide thioglycosides could be the best strategy for achieving the desired tetrasaccharide 1
The tetrasaccharide repeating unit of the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71T was synthesized in good yield using a sequential as well as a one-pot iterative glycosylation approach
Summary
The development of plant-growth-promoting agents has become an attractive area of research in the agricultural sciences to reduce the need for chemical fertilizers, which cause environmental pollution, resistance in plant pathogens as well as high production costs of crops [1,2,3].
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