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 r...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2001-04, Vol.20 (4-7), p.981-983
Main Authors: Molina, José, Maslen, Hannah L., Simons, Claire
Format: Article
Language:English
Subjects:
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
Nucleic Acid Conformation
Nucleosides - chemical synthesis
Nucleosides - chemistry
Oxazoles - chemical synthesis
Oxazoles - chemistry
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Summary: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.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-100002473