C-Nucleoside studies. Part 19. The synthesis of the β-D-xylofuranosyl analogue of formycin

J. Grant Buchanan, Duncan Smith, Richard H. Wightman

Research output: Contribution to journalArticle

Abstract

1-(2,4-Dinitrophenyl)-3-(2,3,5-tri-O-acetyl-ß-D-xylofuranosyl)pyrazole (15), prepared by improved procedures from D-gulonolactone, was treated with ammonium nitrate and trifluoroacetic anhydride in trifluoroacetic acid to give, after deprotection of the pyrazole ring, 4-nitro-3(5)-(2,3,5-tri-O-acetyl- ß-D-xylofuranosyl)pyrazole (17). N-Nitration and cine-substitution with cyanide ion gave 3(5)-cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-ß-D- xylofuranosyl)pyrazole (19) in 66% overall yield; this was elaborated into 7-amino-3-(ß-D-xylofuranosyl)pyrazolo[4,3-d]pyrimidine (3), the xylofuranosyl analogue of the C-nucleoside antibiotic formycin.

Original languageEnglish
Pages (from-to)1267-1271
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1986

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Nucleosides
trifluoroacetic anhydride
Nitration
Trifluoroacetic Acid
Cyanides
Substitution reactions
Ions
Anti-Bacterial Agents
pyrazole
formycin

Cite this

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title = "C-Nucleoside studies. Part 19. The synthesis of the β-D-xylofuranosyl analogue of formycin",
abstract = "1-(2,4-Dinitrophenyl)-3-(2,3,5-tri-O-acetyl-{\ss}-D-xylofuranosyl)pyrazole (15), prepared by improved procedures from D-gulonolactone, was treated with ammonium nitrate and trifluoroacetic anhydride in trifluoroacetic acid to give, after deprotection of the pyrazole ring, 4-nitro-3(5)-(2,3,5-tri-O-acetyl- {\ss}-D-xylofuranosyl)pyrazole (17). N-Nitration and cine-substitution with cyanide ion gave 3(5)-cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-{\ss}-D- xylofuranosyl)pyrazole (19) in 66{\%} overall yield; this was elaborated into 7-amino-3-({\ss}-D-xylofuranosyl)pyrazolo[4,3-d]pyrimidine (3), the xylofuranosyl analogue of the C-nucleoside antibiotic formycin.",
author = "Buchanan, {J. Grant} and Duncan Smith and Wightman, {Richard H.}",
year = "1986",
language = "English",
pages = "1267--1271",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",

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C-Nucleoside studies. Part 19. The synthesis of the β-D-xylofuranosyl analogue of formycin. / Buchanan, J. Grant; Smith, Duncan; Wightman, Richard H.

In: Journal of the Chemical Society, Perkin Transactions 1, 1986, p. 1267-1271.

Research output: Contribution to journalArticle

TY - JOUR

T1 - C-Nucleoside studies. Part 19. The synthesis of the β-D-xylofuranosyl analogue of formycin

AU - Buchanan, J. Grant

AU - Smith, Duncan

AU - Wightman, Richard H.

PY - 1986

Y1 - 1986

N2 - 1-(2,4-Dinitrophenyl)-3-(2,3,5-tri-O-acetyl-ß-D-xylofuranosyl)pyrazole (15), prepared by improved procedures from D-gulonolactone, was treated with ammonium nitrate and trifluoroacetic anhydride in trifluoroacetic acid to give, after deprotection of the pyrazole ring, 4-nitro-3(5)-(2,3,5-tri-O-acetyl- ß-D-xylofuranosyl)pyrazole (17). N-Nitration and cine-substitution with cyanide ion gave 3(5)-cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-ß-D- xylofuranosyl)pyrazole (19) in 66% overall yield; this was elaborated into 7-amino-3-(ß-D-xylofuranosyl)pyrazolo[4,3-d]pyrimidine (3), the xylofuranosyl analogue of the C-nucleoside antibiotic formycin.

AB - 1-(2,4-Dinitrophenyl)-3-(2,3,5-tri-O-acetyl-ß-D-xylofuranosyl)pyrazole (15), prepared by improved procedures from D-gulonolactone, was treated with ammonium nitrate and trifluoroacetic anhydride in trifluoroacetic acid to give, after deprotection of the pyrazole ring, 4-nitro-3(5)-(2,3,5-tri-O-acetyl- ß-D-xylofuranosyl)pyrazole (17). N-Nitration and cine-substitution with cyanide ion gave 3(5)-cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-ß-D- xylofuranosyl)pyrazole (19) in 66% overall yield; this was elaborated into 7-amino-3-(ß-D-xylofuranosyl)pyrazolo[4,3-d]pyrimidine (3), the xylofuranosyl analogue of the C-nucleoside antibiotic formycin.

M3 - Article

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EP - 1271

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

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