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Volumn 63, Issue 23, 1998, Pages 8150-8156

Nucleoside H-phosphonates. 18. Synthesis of unprotected nucleoside 5'- H-phosphonates and nucleoside 5'-H-phosphonothioates and their conversion into the 5'-phosphorothioate and 5'-phosphorodithioate monoesters

Author keywords

[No Author keywords available]

Indexed keywords

5' PHOSPHORODITHIOATE MONOESTER; 5' PHOSPHOROTHIOATE MONOESTER; NUCLEOSIDE 5' H PHOSPHONATE; NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032514991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980491u     Document Type: Article
Times cited : (26)

References (39)
  • 8
    • 0041858495 scopus 로고    scopus 로고
    • Interaction of thymidylate synthase with the 5′-thiophosphates and 5′-H-phosphonates of 2′-deoxyuridine, thymidine and 5-fluoro-2′-deoxyuridine
    • Pfleiderer, W., Rokos, H., Eds.; Blackwell Science: Berlin
    • Golos, B.; Dzik, J. M.; Rode, W.; Jankowska, J.; Kraszewski, A.; Stawiński, J.; Shugar, D. Interaction of thymidylate synthase with the 5′-thiophosphates and 5′-H-phosphonates of 2′-deoxyuridine, thymidine and 5-fluoro-2′-deoxyuridine; In Chemistry and Biology of Pteridines and Folates; Pfleiderer, W., Rokos, H., Eds.; Blackwell Science: Berlin, 1997; pp 423-426.
    • (1997) Chemistry and Biology of Pteridines and Folates , pp. 423-426
    • Golos, B.1    Dzik, J.M.2    Rode, W.3    Jankowska, J.4    Kraszewski, A.5    Stawiński, J.6    Shugar, D.7
  • 12
    • 15444347452 scopus 로고    scopus 로고
    • Studies on synthesis of phosphate analogues utilizing unprotected H-phosphonates, H-phosphonothioates, and H-phosphonodithioates derived from various natural products are currently under investigation in these laboratories
    • Studies on synthesis of phosphate analogues utilizing unprotected H-phosphonates, H-phosphonothioates, and H-phosphonodithioates derived from various natural products are currently under investigation in these laboratories.
  • 13
    • 15444346765 scopus 로고
    • Attempted dithiophosphorylation of unprotected (or partially protected) nucleosides with unsubstituted dithiophosphate dianion in dimethylformamide afforded exclusively mixtures of the corresponding 3′ (5′) nucleoside phosphoromonothioates. See: Dunaway-Mariano, D. Tetrahedron 1976, 32, 2991-2996.
    • (1976) Tetrahedron , vol.32 , pp. 2991-2996
    • Dunaway-Mariano, D.1
  • 20
    • 0001523773 scopus 로고
    • Some Aspects of H-Phosphonate Chemistry
    • Engel, R., Ed.; Marcel Dekker: New York
    • Stawiński, J. Some Aspects of H-Phosphonate Chemistry; In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; pp 377-434.
    • (1992) Handbook of Organophosphorus Chemistry , pp. 377-434
    • Stawiński, J.1
  • 22
    • 15444358058 scopus 로고    scopus 로고
    • 31P NMR and TLC analysis)
    • 31P NMR and TLC analysis).
  • 23
    • 15444354852 scopus 로고    scopus 로고
    • 31P NMR and TLC analysis)
    • 31P NMR and TLC analysis).
  • 26
    • 15444355925 scopus 로고    scopus 로고
    • The reaction was carried out on a small scale and the product isolated by paper chromatography
    • The reaction was carried out on a small scale and the product isolated by paper chromatography.
  • 27
    • 15444355186 scopus 로고    scopus 로고
    • note
    • For example, dithymidine (3′-5′) H-phosphonate (0.25 mmol/2 mL) in the presence of triethylamine (2 equiv) underwent oxidation with sulfur (2 equiv) to the corresponding dinucleoside phosphorothioate within 1 min in DMF or MeOH, ca. 10 min in pyridine, ca. 40 min in dioxane or toluene, and ca. 90 min in carbon disulfide. When triethylamine was replaced by diisopropylamine or DBU, the reaction in dioxane went to completion within 10 and 1 min, respectively (R. Wallin and J. Stawiński, unpublished results).
  • 31
    • 15444352882 scopus 로고    scopus 로고
    • 31P NMR spectroscopy
    • 31P NMR spectroscopy.
  • 32
    • 15444359728 scopus 로고    scopus 로고
    • 31P NMR experiment)
    • 31P NMR experiment).
  • 34
    • 15444352137 scopus 로고    scopus 로고
    • Upon addition of triethylamine to a solution of sulfur in Pyridine, a deep yellow color, characteristic for polysulfides, developed. This disappeared during the course of the reaction with phosphite 11
    • Upon addition of triethylamine to a solution of sulfur in Pyridine, a deep yellow color, characteristic for polysulfides, developed. This disappeared during the course of the reaction with phosphite 11.
  • 36
    • 15444341799 scopus 로고    scopus 로고
    • note
    • HP = 659 and 660 Hz) upon further addition of the silylating agent or triethylamine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.