Synthesis of a Novel Pyrazolo[1, 5-C]Pyrimidine C-Nucleoside and Conformational Analysis By NMR Spectroscopy

Isopropylidenation of [4-methoxycarbonyl-5-(β-D-ribofuranosyl)-1H-pyrazol-3-yl]acetamide (1a) followed by the acidic cleavage of the sugar acetonide afforded 3-methoxycarbonyl-7, 7-dimethyl-2-(β-D-ribofuranosyl)-4H, 7H-pyrazolo[1,5-c] pyrimidine-5(6H)-one (2b), the structure of which was established...

Full description

Saved in:
Bibliographic Details
Published inNucleosides & nucleotides Vol. 18; no. 11-12; pp. 2601 - 2611
Main Authors Prhavc, Marija, Plavec, Janez, Kobe, Joźe, Leban, Ivan, Giester, Gerald
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.11.1999
Marcel Dekker Inc
Subjects
Biochemistry & Molecular Biology
Life Sciences & Biomedicine
Science & Technology
NUCLEOTIDES
PSEUDOROTATIONAL EQUILIBRIUM
PENTOFURANOSE MOIETY
BOND
COUPLING-CONSTANTS
DRIVE
Online AccessGet full text

Cover

More Information
Summary:Isopropylidenation of [4-methoxycarbonyl-5-(β-D-ribofuranosyl)-1H-pyrazol-3-yl]acetamide (1a) followed by the acidic cleavage of the sugar acetonide afforded 3-methoxycarbonyl-7, 7-dimethyl-2-(β-D-ribofuranosyl)-4H, 7H-pyrazolo[1,5-c] pyrimidine-5(6H)-one (2b), the structure of which was established unequivocally by X-ray structure analysis of the monocrystals. Compounds 1a and 2b have 75% and 70% preference for the N-type puckering between C3′-endo and C3′-endo-C4′-exo forms, and a great preference of 69% and 74% for γ + rotamers in solution, respectively.
ISSN:0732-8311
2332-3892
DOI:10.1080/07328319908044629