Journal of Organic Chemistry 2009-03-20

Additive Pummerer reaction of 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal: a high-yield and beta-selective entry to 4'-thioribonucleosides.

Kazuhiro Haraguchi, Hiromitsu Matsui, Shin Takami, Hiromichi Tanaka

Index: J. Org. Chem. 74(6) , 2616-9, (2009)

Full Text: HTML

Abstract

Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac(2)O/TMSOAc/BF(3) x OEt(2) in CH(2)Cl(2), the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly beta-selective glycosyl donor in the Vorbruggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-beta-D-ribofuranosyl derivatives of uracil, thymine, N (4) -acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the beta-selective synthesis of 4'-thio-C-ribonucleosides.

Related Compounds

Related Articles:

Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition

2009-01-01

[Bioorg. Med. Chem. Lett. 19 , 6433-6, (2009)]

The synthesis of novel fluorescent purine analogues modified by azacrown ether at C6

2010-01-01

[Bioorg. Med. Chem. Lett. 20(10) , 3098-102, (2010)]

Evidence for Watson-Crick and not Hoogsteen or wobble base pairing in the selection of nucleotides for insertion opposite pyrimidines and a thymine dimer by yeast DNA pol eta.

2005-03-29

[Biochemistry 44(12) , 4850-60, (2005)]

Asymmetric synthesis of novel thioiso dideoxynucleosides with exocyclic methylene as potential antiviral agents.

2004-04-30

[J. Org. Chem. 69(9) , 3208-11, (2004)]

Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents.

2007-05-01

[Bioorg. Med. Chem. Lett. 17 , 2470-3, (2007)]

More Articles...