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Volumn 38, Issue 24, 1997, Pages 4215-4218

Isonucleosides by Michael addition of pyrimidine bases on 2,6-disubstituted 2H-pyran-3(6H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PYRAN DERIVATIVE; PYRIMIDINE DERIVATIVE;

EID: 0343035768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00859-9     Document Type: Article
Times cited : (12)

References (37)
  • 8
    • 0030021563 scopus 로고    scopus 로고
    • and references therein
    • c) Konkel, M. J.; Vince, R. Tetrahedron 1996, 52, 799-808 and references therein.
    • (1996) Tetrahedron , vol.52 , pp. 799-808
    • Konkel, M.J.1    Vince, R.2
  • 22
    • 0028815216 scopus 로고
    • The Ferrier reaction favors the obtention of α-anomer, chromatographically less polar than the corresponding 2β-anomer (Doboszewski, B.; Blaton, N.; Herdewijn, P. Tetrahedron Lett. 1995, 36, 1321-1324). Isopropanol has the advantage to give after hydrolysis the α-anomer as a solid directly purified by recrystallization (mp = 103 °C).
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1321-1324
    • Doboszewski, B.1    Blaton, N.2    Herdewijn, P.3
  • 24
    • 20544432179 scopus 로고
    • Paquette, L. A. Ed.; John Wiley and Sons, Inc.; Chichester
    • Sweeney, J.; Perkins, G. In Reagents for Organic Synthesis; Paquette, L. A. Ed.; John Wiley and Sons, Inc.; Chichester, 1995; pp. 5315-5319.
    • (1995) Reagents for Organic Synthesis , pp. 5315-5319
    • Sweeney, J.1    Perkins, G.2
  • 26
    • 0030184237 scopus 로고    scopus 로고
    • Only N-1 nucleosides were observed without N-3 or O-alkylation by-products (Luyten, I.; Herdewijn, P. Tetrahedron 1996, 52, 9249-9262.)
    • (1996) Tetrahedron , vol.52 , pp. 9249-9262
    • Luyten, I.1    Herdewijn, P.2
  • 27
    • 0342912766 scopus 로고    scopus 로고
    • note
    • General procedure for the preparation of 9-15 : In a flask (100 mL) equipped with a magnetic stirrer and connected to a nitrogen atmosphere, a mixture of nucleobase (3 mmol) in dry acetonitrile (40 mL) was introduced. N, O-bis(trimethylsilyl) acetamide (BSA) (2.48 mL, 10 mmol) was added via a syringe and the suspension stirred at r.t. until complete dissolution. Pyran-3-one 1-3 (3 mmol) was added over 2 min followed by TMSOTf (1.3 mL, 7 mmol) via the syringe. The resulting solution was stirred for 2 h at R.T., then water (60 mL) was added. After concentration in vacuo, the aqueous solution was partitioned with EtOAc. After usual work-up, the residue consisted of crude 9-15.
  • 28
    • 0343347995 scopus 로고    scopus 로고
    • note
    • 13C)-COSY spectra to establish the the relationship of H-atoms in compounds 23-27. No racemization at C-5′ occurs (Eu shift reagent, det. limit ca. 95 % e.e.).
  • 37
    • 0343347994 scopus 로고    scopus 로고
    • note
    • 6 : C, 53.49; H, 7.05; N, 8.91%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.