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Volumn 49, Issue 42, 2008, Pages 6068-6070

De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-HNA)

Author keywords

1,6 Anhydro l sugars; Domino reactions; HNA; Nucleosides analogues; Oligonucleotides

Indexed keywords

1,5 ANHYDROHEXITOL NUCLEOSIDE DERIVATIVE; 1,6 ANHYDROSUGAR DERIVATIVE; CARBOHYDRATE DERIVATIVE; LEVO ANHYDROHEXITOL NUCLEOSIDE DERIVATIVE; LEVO HEXITOL NUCLEIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 50549094586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.159     Document Type: Article
Times cited : (18)

References (27)
  • 15
    • 34548185629 scopus 로고    scopus 로고
    • Compound 5 has been prepared starting from our heterocyclic homologating agent. See:. Paquette L.A. (Ed), John Wiley & Sons, New York, US 10.1002/047084289X.rn00831
    • Compound 5 has been prepared starting from our heterocyclic homologating agent. See:. Guaragna A., Pedatella S., and Palumbo G. In: Paquette L.A. (Ed). e-Encyclopedia of Reagents for Organic Synthesis (e-EROS) (2008), John Wiley & Sons, New York, US 10.1002/047084289X.rn00831
    • (2008) e-Encyclopedia of Reagents for Organic Synthesis (e-EROS)
    • Guaragna, A.1    Pedatella, S.2    Palumbo, G.3
  • 17
    • 50549087386 scopus 로고    scopus 로고
    • note
    • 2) and TMSOTf were attempted, the last one successfully driving the reaction in 2 h at 0 °C (78% yield).
  • 20
    • 50549090741 scopus 로고    scopus 로고
    • note
    • DBU was preferred to other commonly used bases, such as NaH or LiH, because not strictly anhydrous conditions were required.
  • 21
    • 50549092771 scopus 로고    scopus 로고
    • note
    • After chromatographic purification a UV detectable byproduct was also isolated (10% yield): complete NMR characterization (COSY, HMBC, HSQC-TOCSY) unambiguously determined its structure as the bis-alkylated thymine, corresponding to the molecule reported below:{A figure is presented}.
  • 25
    • 50549096492 scopus 로고    scopus 로고
    • note
    • During the reaction, an inseparable mixture of two products was formed (TLC). Although an unambiguous identification of the structure was not possible, a second alkylation on the nucleobase moiety is assumed to have occurred, as already reported elsewhere [see Ref. 21].
  • 26
    • 50549083090 scopus 로고    scopus 로고
    • note
    • 5: C, 51.56; H, 6.29; N, 10.93. Found: C, 51.38; H, 6.31; N, 10.97.
  • 27
    • 50549085877 scopus 로고    scopus 로고
    • note
    • 3: C, 49.81; H, 5.70; N, 26.40. Found: C, 49.96; H, 5.72; N, 26.48.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.