- Synthesis of 9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione
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A synthesis of 9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione was performed by desulfurization of 2'-deoxy-6-thioguanine to give 2-amino-9-(2- deoxy-β-D-ribofuranosyl)purine, diazotization with chloride replacement to give 2-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine, and the replacement of chloride with sulfur using thiolacetic acid and deacetylation.
- Rappaport, Harry P.
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- One-flask syntheses of 6-thioguanosine and 27′-deoxy-6-thioguanosine
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We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.
- Kung, Pei-Pei,Jones, Roger A.
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- A new approach to the synthesis of 2-aminopurine-2'-deoxyriboside via tri- n-butyltin hydride reduction
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A simple conversion of guanosine to 2-aminopurine-2'-deoxyriboside is described. Following the synthesis of the 2'-phenoxythiocarbonyl derivative of 6-chloroguanosine, 2-aminopurine-2'-deoxyriboside can be prepared by simultaneous reduction of both the 6-
- Schmidt,Cech
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p. 1445 - 1452
(2007/10/03)
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- Chemical and enzymatic synthesis of 2'-deoxy-iso-inosine and its incorporation into DNA
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Two procedures for the preparation of 2'-deoxy-iso-inosine (1) are presented. Synthesis of 3'-phosphoramidite (7) and 3'-phosphonate (8) derivatives are described, as well as an oligodeoxynucleotide containing iso-I.
- Beaussire,Pochet
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p. 805 - 808
(2007/10/02)
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- 2'-Deoxyisoinosine: Synthesis of a highly fluorescent nucleoside and its incorporation into oligonucleotides
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The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'- dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.
- Seela,Chen
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p. 863 - 866
(2007/10/02)
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- Antiviral agents
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Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.
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