Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI.
Тип публикации: Journal Article
Дата публикации: 2011-12-08
scimago Q3
wos Q3
БС2
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
3409411
General Chemistry
Drug Discovery
General Medicine
Краткое описание
The reaction of 4-ethoxy-1-(3, 5-O-tetraisopropyldisiloxanyl-1, 3-diyl-β-D-erythro-pentofuran-2-ulosyl)-2(1H)-pyrimidinone (11) with various organometallic reagents yielded corresponding 2'-branched-chain sugar pyrimidine nucleosides. Only in the reactions with MeMgBr and EtMgBr was the more hindered β-attack observed to afford and 2'-alkyl ribofuranosides (13a, b). In the reaction of 11 with MeLi, Me3, Al, or PhMgBr, 2'-methyl or phenyl arabinosides (12a, b, c)were obtained stereoselectively. Conversion of these pyrimidine nucleosides into cytosine derivatives is also described and their antileukemic and antiviral activities are discussed.
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Matsuda A. et al. Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 36. No. 3. pp. 945-953.
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Matsuda A., ITOH H., TAKENUKI K., Sasaki T., UEDA T. Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 36. No. 3. pp. 945-953.
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TY - JOUR
DO - 10.1248/cpb.36.945
UR - https://doi.org/10.1248/cpb.36.945
TI - Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI.
T2 - Chemical and Pharmaceutical Bulletin
AU - Matsuda, Akira
AU - ITOH, Hiroko
AU - TAKENUKI, Kenji
AU - Sasaki, Takuma
AU - UEDA, Tohru
PY - 2011
DA - 2011/12/08
PB - Pharmaceutical Society of Japan
SP - 945-953
IS - 3
VL - 36
PMID - 3409411
SN - 0009-2363
SN - 1347-5223
ER -
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@article{2011_Matsuda,
author = {Akira Matsuda and Hiroko ITOH and Kenji TAKENUKI and Takuma Sasaki and Tohru UEDA},
title = {Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {36},
publisher = {Pharmaceutical Society of Japan},
month = {dec},
url = {https://doi.org/10.1248/cpb.36.945},
number = {3},
pages = {945--953},
doi = {10.1248/cpb.36.945}
}
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MLA
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Matsuda, Akira, et al. “Alkyl addition reaction of pyrimidine 2'-ketonucleosides: synthesis of 2'-branched-chain sugar pyrimidine nucleosides (nucleosides and nucleotides. LXXXI..” Chemical and Pharmaceutical Bulletin, vol. 36, no. 3, Dec. 2011, pp. 945-953. https://doi.org/10.1248/cpb.36.945.