Methyl 5-O-benzoyl-2,3-oxazole-D-ribofuranoside: a useful intermediate for the synthesis of conformationally restrained nucleosides.
The synthesis of methyl 5-O-benzoyl-2,3-oxazole-D-ribofuranoside, a tetrahydrofuro [3,4-d]oxazole is described. The key step involves the reaction of methyl 3-amino-3-deoxy-5-O-benzoyl-D-ribofuranoside with N,N-dimethylformamide dimethyl acetal with cyclisation to the 2,3-oxazole via a prototropic rearrangement-elimination reaction.
Molina
J
J
Medicinal Chemistry Division, Welsh School of Pharmacy, Cardiff University, King Edward VII Avenue, Cardiff CF10 3XF, United Kingdom.
Maslen
H L
HL
Simons
C
C
D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
D009005:Monosaccharides; D009705:Nucleosides; D010080:Oxazoles; C442712:methyl 5-O-benzoyl-2,3-oxazole-ribofuranoside