Organic Letters
Organic Letters
5 years ago

Pentavalent Bismuth as a Universal Promoter for S-Containing Glycosyl Donors with a Thiol Additive

Pentavalent Bismuth as a Universal Promoter for S-Containing Glycosyl Donors with a Thiol Additive
Nicola L. B. Pohl, Daniel E. K. Kabotso
S-Propyl glycosides of less activated sugars, such as peracetylated carbohydrates and uronic acid esters that could not previously be activated with triphenylbismuth ditriflate alone, were found to be glycosylated in the presence of propanethiol as an additive in under 3 h. This newly developed protocol was also found to be effective in promoting glycosylation of neutral and uronic acid esters of S-phenyl, S-thiazolinyl, S-benzoxazolyl, and S-adamantyl glycosides as well as sialic acid.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02080

DOI: 10.1021/acs.orglett.7b02080

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