Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis.
The chemo- and regioselective TEMPO/BAIB-mediated oxidation of 2,6- and 3,6-dihydroxy 1-thio glycopyranosides to the corresponding 1-thio uronic acid lactones is described. These locked 1-thio glycuronides can directly be used as donors in glycosidation reactions using the Ph(2)SO/Tf(2)O reagent system. Alternatively, selective opening of the lactone bridge liberates a hydroxyl function for ensuing glycosylations.
van den Bos
Leendert J
LJ
Leiden Institute of Chemistry, Leiden University, The Netherlands.
Litjens
Remy E J N
RE
van den Berg
Richard J B H N
RJ
Overkleeft
Herman S
HS
van der Marel
Gijsbert A
GA
D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014574:Uronic Acids / Q000138:chemical synthesis*
D007783:Lactones; D009844:Oligosaccharides; D014574:Uronic Acids