Concise syntheses of D-desosamine, 2-thiopyrimidinyl desosamine donors, and methyl desosaminide analogues from D-glucose.
A concise synthesis of d-desosamine has been accomplished in five steps and in 15% overall yield from methyl alpha-d-glucopyranoside. Desosamine was then transformed into two known 2-thiopyrimidinyl donors (Woodward and Tatsuta donors), each in two steps. Finally, analogues of methyl desosaminide at the C-3 position were prepared (3-pyrrolidino, 3-piperidino, 3-morpholino) from a common 2,3-anhydrosugar intermediate.
Velvadapu
Venkata
V
Temple University, Department of Chemistry, Philadelphia, PA 19122, United States.
Andrade
Rodrigo B
RB
D000606:Amino Sugars / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D008757:Methylglucosides / Q000737:chemistry
D000606:Amino Sugars; D008757:Methylglucosides; C110125:desosamine; C027020:methylglucoside; D005947:Glucose