Abstract
Syntheses of acyl protected exo-mannal derivatives were developed starting from O-peracylated mannopyranoses via the corresponding anhydro-aldose tosylhydrazones under modified Bamford–Stevens conditions. The synthesis of analogous O-peralkylated (benzylated and isopropylenated) derivatives was carried out from pyranoid and furanoid mannonolactones using methylene transfer reagents. Photoinitiated thiol–ene additions of these exo-mannals resulted in the corresponding C-(mannopyranosyl/mannofuranosyl)methyl sulfides in medium to good yields with exclusive regio- and β(d) stereoselectivities.
Highlights
D-Mannose occurs in microbes, plants, animals in free form, but more o en as a component of glycans or glycoproteins
The mannose binding lectins (MBL) of the human cells play a central role in innate immunity by the interaction with surface sugars of a wide series of microorganisms, but this speci c interaction can be used for selective delivery of anti-cancer drugs, using glycosylated bioconjugates.[8,9,10]
We have developed a simple method for the preparation of exo-glycals with ester type protection of
Summary
D-Mannose occurs in microbes, plants, animals in free form, but more o en as a component of glycans or glycoproteins. The O-glycosidic bond in natural glycosides is characterized with low hydrolytic and/or enzymatic stability but by replacing the glycosidic oxygen with other atoms (C, N, S)[11] or groups (S–S, S–Se, SO2–N, and N–C(]O)–N),[12] more stable molecules can be synthesized with similar biological activity. These molecules are the glycomimetics,[11] which are frequently used as leads of drug discovery
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