185836-58-2Relevant articles and documents
A novel donor for the synthesis of 2-deoxy-β-glycosides
Marzabadi, Cecilia H.,Franck, Richard W.
, p. 2651 - 2652 (1996)
Vinyl glycoside 2, available in two steps from tribenzyl glucal, is found to be an excellent glycosyl donor for the synthesis of 2-deoxy-β-glycosides.
Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides
Franck, Richard W.,Marzabadi, Cecilia H.
, p. 2197 - 2208 (2007/10/03)
Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol acceptors leads to the formation of β-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-β-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.
