1,6-Anhydro-β-D-glucopyranose derivatives as glycosyl donors for thioglycosidation reactions

doi:10.1039/P19900001677

Paper

1,6-Anhydro-β-D-glucopyranose derivatives as glycosyl donors for thioglycosidation reactions

Published 1990 · Lai-Xi Wang, N. Sakairi, H. Kuzuhara

Journal of The Chemical Society-perkin Transactions 1

UNKNOWN SJR score

31

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0

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Abstract

1,6-Anhydro derivatives of D-glucopyranose, maltose, and maltotriose reacted at room temperature with trimethylsilylated benzenethiol (2) and cyclohexanethiol (3) in the presence of zinc iodide (Znl2) or trimethylsilyl triflate (TMSOTf), giving the corresponding thioglycosides with predominance of one anomer in high yield. 1,6-Anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (1) condensed with a more complex thiol derivative, methyl 2,3,6-tri-O-benzyl-4-thio-4-S-trimethylsilyl-α-D-glucopyranoside (19), to give the 4-thiomaltose derivative (20), whereas no condensation took place between the 1,6-anhydro disaccharide homologue (21) and thiol derivative (19). The difference in reactivity between 1,6-anhydro mono- and di-saccharides was utilized for a specific cross-coupling reaction.

Study Snapshot

1,6-anhydro--D-glucopyranose derivatives can be used as glycosyl donors for thioglycosidation reactions, with high yields and potential for cross-coupling reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

1,6-Anhydro-β-D-glucopyranose derivatives as glycosyl donors for thioglycosidation reactions

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References

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Citations

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