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Volumn 67, Issue 26, 2002, Pages 9331-9339

Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYST SELECTIVITY; DERIVATIVES; ENZYMES; HYDROLYSIS; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 0037184769     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020483k     Document Type: Article
Times cited : (37)

References (34)
  • 1
    • 0000855125 scopus 로고
    • Cytidine analogues
    • Chabner, B. A., Longo, D. L., Eds.; J. B. Lippincott Co.: Philadelphia, PA
    • Chabner, B. A. Cytidine analogues. In Cancer Chemotherapy: Principals and Practice, 2nd Ed.; Chabner, B. A., Longo, D. L., Eds.; J. B. Lippincott Co.: Philadelphia, PA, 1995.
    • (1995) Cancer Chemotherapy: Principals and Practice, 2nd Ed.
    • Chabner, B.A.1
  • 5
    • 0029036336 scopus 로고
    • and references therein
    • (a) McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131-7148 and references therein.
    • (1995) Tetrahedron , vol.51 , pp. 7131-7148
    • McEldoon, W.L.1    Wiemer, D.F.2
  • 8
    • 12244272081 scopus 로고    scopus 로고
    • note
    • These authors also assigned the major phosphonate derived from phosphite addition to a cytidine aldehyde as the 5′R isomer, although no data for that compound were included in their preliminary report.
  • 9
    • 0036020844 scopus 로고    scopus 로고
    • Sendai, Japan, August
    • Presented in part at the International Conference on Phosphorus Chemistry, Sendai, Japan, August 2001. Chen, X.; Jung, K.; Wiemer, D. F.; Wiemer, A. J.; Hohl, R. J. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 1783-1786.
    • (2001) International Conference on Phosphorus Chemistry
  • 10
    • 0036020844 scopus 로고    scopus 로고
    • Presented in part at the International Conference on Phosphorus Chemistry, Sendai, Japan, August 2001. Chen, X.; Jung, K.; Wiemer, D. F.; Wiemer, A. J.; Hohl, R. J. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 1783-1786.
    • (2002) Phosphorus, Sulfur, Silicon Relat. Elem. , vol.177 , pp. 1783-1786
  • 17
    • 12244253677 scopus 로고    scopus 로고
    • note
    • These assignments also are consistent with the stereochemical outcome of allylation reactions conducted with aldehydes 8 and 18. Reaction of aldehyde 8 with allyltrimethylsilane gave only the 5′R adduct while reaction of aldehyde 18 under the same conditions gave only the 5′S product, as shown by single-crystal diffraction analysis. Furthermore, allylation of aldehyde 23 with allyltrimethylsilane gave only the 5′R adduct, as established by diffraction analysis and also parallel to the course of phosphite addition. Unpublished results from X. Chen and D. F. Wiemer.
  • 30
    • 12244264115 scopus 로고    scopus 로고
    • note
    • 2 from -78 °C to room temperature gave the R adduct as its trimethylsilyl derivative in 64% yield. After hydrolysis of the silyoxy groups, the C-5′ stereochemistry was confirmed by comparison with compound 23a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.