Journal
RSC ADVANCES
Volume 10, Issue 57, Pages 34825-34836Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra07115c
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Funding
- National Research, Development and Innovation Office of Hungary [K109450, K132870, FK128766]
- EU - European Regional Development Fund [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004]
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Syntheses of acyl protectedexo-mannal derivatives were developed starting fromO-peracylated mannopyranosesviathe corresponding anhydro-aldose tosylhydrazones under modified Bamford-Stevens conditions. The synthesis of analogousO-peralkylated (benzylated and isopropylenated) derivatives was carried out from pyranoid and furanoid mannonolactones using methylene transfer reagents. Photoinitiated thiol-ene additions of theseexo-mannals resulted in the correspondingC-(mannopyranosyl/mannofuranosyl)methyl sulfides in medium to good yields with exclusive regio- and beta(d) stereoselectivities.
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