TY - JOUR
T1 - Reinvestigation of the synthesis of 1-deazauridine
AU - Jen, Cheng Hung
AU - Chien, Tun Cheng
N1 - Funding Information:
Received 23 November 2009; accepted 9 March 2010. This work was supported by Research Grant 96-2113-M-003-004 from the National Science Council, Taiwan. We are grateful to the National Center for High-Performance Computing of Taiwan for the electronic resources and facilities. Address correspondence to Tun-Cheng Chien, Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan. E-mail: tcchien@ntnu.edu.tw
Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2010/7
Y1 - 2010/7
N2 - A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(-d-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization. The effort concluded that the synthesis of 1-deazauridine remained unachieved.
AB - A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(-d-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization. The effort concluded that the synthesis of 1-deazauridine remained unachieved.
KW - 1-deazauridine
KW - 2,6-dimethoxypyridine
KW - C-nucleoside
KW - d-ribonolactone
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U2 - 10.1080/15257771003762170
DO - 10.1080/15257771003762170
M3 - Article
C2 - 20589571
AN - SCOPUS:77954308588
VL - 29
SP - 523
EP - 534
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
SN - 1525-7770
IS - 7
ER -