Synthesis of 5-hydroxy-2-(β- d-ribofuranosyl)pyran-4-one from a pyranulose glycoside

The synthesis of 5-hydroxy-2-(β- d-ribofuranosyl)pyran-4-one ( 9) is described. Treatment of pyranulose glycoside with bromine in carbon tetrachloride afforded brompyranulose glycoside in 90% yield. The reaction of (6 S)- and (6 R)-4-bromo-6-hydroxy-6-(2,3,5-tri- O-benzoyl-β- d-ribofuranosyl)-6 H-py...

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Published in:Carbohydrate research 1999-05, Vol.318 (1), p.180-185
Main Authors: Kanazawa, Shigeyuki, Mizuno, Souhei, Yamauchi, Rie, Nishimura, Natsu, Maeba, Isamu
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
C-Nucleoside
Chromones - chemistry
Glycosides
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Oxazoles - chemistry
Pyran-4-one
Pyranulose glycoside
Pyridazin-4-one
Pyrones - chemical synthesis
Pyrones - chemistry
Ribose - analogs & derivatives
Ribose - chemical synthesis
Ribose - chemistry
Spectrometry, Mass, Fast Atom Bombardment
Synthesis
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Summary:The synthesis of 5-hydroxy-2-(β- d-ribofuranosyl)pyran-4-one ( 9) is described. Treatment of pyranulose glycoside with bromine in carbon tetrachloride afforded brompyranulose glycoside in 90% yield. The reaction of (6 S)- and (6 R)-4-bromo-6-hydroxy-6-(2,3,5-tri- O-benzoyl-β- d-ribofuranosyl)-6 H-pyran-3-one ( 2) in acidic media was examined with the following results: the reaction of 2 with trifluoroacetic acid (TFA) in dioxane afforded a mixture of 5-hydroxy-2-(2,3,5-tri- O-benzoyl-β- d-ribofuranosyl)pyran-4-one ( 3) and its furan derivative 5-hydroxy-2-{5-(benzoyloxy)methyl]furan-2-yl}pyran-4-one ( 4), but the use of hydrochloric acid formed the bromofurfural, 3-bromo-5-(2,3,5-tri- O-benzoyl-β- d-ribofuranosyl)-2-furancarboxyaldehyde only. Acetylation of a mixture ( 3 and 4) with acetic anhydride facilitated product separation to give the corresponding acetates 5-acetoxy-2-(2,3,5-tri- O-benzoyl-β- d-ribofuranosyl)pyran-4-one ( 5) and 5-acetoxy-2-{5-[(benzoyloxy)methyl]furan-2-yl}pyran-4-one ( 6). Treatment of 5 with hydrazine afforded 3-hydroxymethyl-6-(β- d-ribofuranosyl)-1 H-pyridazin-4-one in 43% yield. Debenzoylation of 5 with aq ammonia gave 9 in 50% yield.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(99)00098-1