Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf

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Abstract

(Chemical Equation Presented) A wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable α/β selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.

Original languageEnglish (US)
Pages (from-to)9767-9770
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number24
DOIs
StatePublished - Dec 19 2008

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Glycosylation
Functional groups
Polymers
Alcohols
Molecules
p-tolylsulfenyl trifluoromethanesulfonate

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf. / Kurosu, Michio; Li, Kai.

In: Journal of Organic Chemistry, Vol. 73, No. 24, 19.12.2008, p. 9767-9770.

Research output: Contribution to journalArticle

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