Nucleosides 2:: Synthesis and properties of 3,4-diaryl-4,5-dihydro-1-(β-D-ribofuranosyl)-1,2,4-triazole-5-thiones

被引：10
|
作者：
Mosselhi, MAN [1 ]
机构：
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
来源：
NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 09期
关键词：
D O I：
10.1080/07328319908044863
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
3,4-Diaryl-4,5-dihydro-1,2,4-triazole-5-thiones, (1a-c) were silylated to give compounds (2a-c) which were condensed with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (3) in the presence of trimethylsilyl trifluoromethane sulfonate to afford the corresponding nucleosides 4a-c. Treatment of 4a-c with sodium methoxide in methanol at room temperature afforded the debenzoylated nucleosides 5a-c. The reaction of 5a with acetone in the presence of p-toluenesulfonic acid gave the 2', 3'-isopropylidene derivative (6a). Phosphorylation of 6a with phosphoryl chloride and triethylphosphate followed by treatment with barium hydroxide afforded barium 3,4-diphenyl-4,5-dihydro(beta-D-ribofuranosyl)-1,2,4-triazole-5-thione-5'- monophosphate, which gave after lyophilization the free acid (7a).
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页码：2043 / 2049
页数：7
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