Studies on the interconversion of 2,3'-anhydro-1-β-D-xylofuranosyluracil and 2,2'-anhydro-1-β-D-arabinofuranosyluracil

J. Grant Buchanan, David R. Clark

Research output: Contribution to journalArticle

Abstract

2,3'-Anhydro-1-ß-D-xylofuranosyluracil (10) is converted, reversibly, into 2,2'-anhydro-1-ß-D-arabinofuranosyluracil (1) in the presence of sodium tert-butoxide. The reaction probably involves 2',3'-anhydrouridine as an intermediate and equilibrium is strongly in favour of 1. The behaviour of 1 and 10 towards sodium hydroxide and sodium methoxide is described. Reaction of 3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofuranosyl chloride with monochloromercuri-4-ethoxy-2(lH)-pyrimidinone afforded crystalline 1-(3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofura-nosyl)uraci l (24) in 57% yield. Alkaline methanolysis of 24 gave crystalline 1-(3-azido-3-deoxy-ß-D-xylofuranosyl)uracil, which yielded 1-(3-amino-3-deoxy-ß-D-xylofuranosyl)uracil (27) on hydrogenation. Deamination of 27 with nitrous acid gave mainly uracil (55%) and not the epoxide 5 or compounds derived from it. © 1979.

Original languageEnglish
Pages (from-to)331-341
Number of pages11
JournalCarbohydrate Research
Volume68
Issue number2
Publication statusPublished - Feb 1979

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uracil
sodium
methanolysis
deamination
hydrogenation
sodium hydroxide
epoxides
chlorides
acids

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title = "Studies on the interconversion of 2,3'-anhydro-1-β-D-xylofuranosyluracil and 2,2'-anhydro-1-β-D-arabinofuranosyluracil",
abstract = "2,3'-Anhydro-1-{\ss}-D-xylofuranosyluracil (10) is converted, reversibly, into 2,2'-anhydro-1-{\ss}-D-arabinofuranosyluracil (1) in the presence of sodium tert-butoxide. The reaction probably involves 2',3'-anhydrouridine as an intermediate and equilibrium is strongly in favour of 1. The behaviour of 1 and 10 towards sodium hydroxide and sodium methoxide is described. Reaction of 3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-{\ss}-D-xylofuranosyl chloride with monochloromercuri-4-ethoxy-2(lH)-pyrimidinone afforded crystalline 1-(3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-{\ss}-D-xylofura-nosyl)uraci l (24) in 57{\%} yield. Alkaline methanolysis of 24 gave crystalline 1-(3-azido-3-deoxy-{\ss}-D-xylofuranosyl)uracil, which yielded 1-(3-amino-3-deoxy-{\ss}-D-xylofuranosyl)uracil (27) on hydrogenation. Deamination of 27 with nitrous acid gave mainly uracil (55{\%}) and not the epoxide 5 or compounds derived from it. {\circledC} 1979.",
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Studies on the interconversion of 2,3'-anhydro-1-β-D-xylofuranosyluracil and 2,2'-anhydro-1-β-D-arabinofuranosyluracil. / Buchanan, J. Grant; Clark, David R.

In: Carbohydrate Research, Vol. 68, No. 2, 02.1979, p. 331-341.

Research output: Contribution to journalArticle

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N2 - 2,3'-Anhydro-1-ß-D-xylofuranosyluracil (10) is converted, reversibly, into 2,2'-anhydro-1-ß-D-arabinofuranosyluracil (1) in the presence of sodium tert-butoxide. The reaction probably involves 2',3'-anhydrouridine as an intermediate and equilibrium is strongly in favour of 1. The behaviour of 1 and 10 towards sodium hydroxide and sodium methoxide is described. Reaction of 3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofuranosyl chloride with monochloromercuri-4-ethoxy-2(lH)-pyrimidinone afforded crystalline 1-(3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofura-nosyl)uraci l (24) in 57% yield. Alkaline methanolysis of 24 gave crystalline 1-(3-azido-3-deoxy-ß-D-xylofuranosyl)uracil, which yielded 1-(3-amino-3-deoxy-ß-D-xylofuranosyl)uracil (27) on hydrogenation. Deamination of 27 with nitrous acid gave mainly uracil (55%) and not the epoxide 5 or compounds derived from it. © 1979.

AB - 2,3'-Anhydro-1-ß-D-xylofuranosyluracil (10) is converted, reversibly, into 2,2'-anhydro-1-ß-D-arabinofuranosyluracil (1) in the presence of sodium tert-butoxide. The reaction probably involves 2',3'-anhydrouridine as an intermediate and equilibrium is strongly in favour of 1. The behaviour of 1 and 10 towards sodium hydroxide and sodium methoxide is described. Reaction of 3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofuranosyl chloride with monochloromercuri-4-ethoxy-2(lH)-pyrimidinone afforded crystalline 1-(3-azido-3-deoxy-2,5-di-O-p-nitrobenzoyl-ß-D-xylofura-nosyl)uraci l (24) in 57% yield. Alkaline methanolysis of 24 gave crystalline 1-(3-azido-3-deoxy-ß-D-xylofuranosyl)uracil, which yielded 1-(3-amino-3-deoxy-ß-D-xylofuranosyl)uracil (27) on hydrogenation. Deamination of 27 with nitrous acid gave mainly uracil (55%) and not the epoxide 5 or compounds derived from it. © 1979.

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