Synthesis of a six-carbon sialic acid using an indium-mediated coupling.
[reaction: see text] The synthesis of a six-carbon truncated sialic acid is described. A key step in the synthesis was an indium-mediated allyl addition to a serine-derived aldehyde. Careful choice of protecting groups was found to be necessary in order to prevent unwanted side reactions throughout the sequence. The truncated sialic acid was obtained in a form suitable for activation as a glycosyl donor.
Chappell
M D
MD
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Halcomb
R L
RL
D000447:Aldehydes / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D012694:Serine / Q000737:chemistry; D012794:Sialic Acids / Q000138:chemical synthesis*
D000447:Aldehydes; D012794:Sialic Acids; D007204:Indium; D012694:Serine