메뉴 건너뛰기




Volumn 65, Issue 31, 2009, Pages 6008-6016

Nucleophilic substitution approach to 4′-substituted thymidines by employing 4′-benzenesulfonyl leaving group

Author keywords

Benzenesulfonyl leaving group; Nucleophilic substitution; Organoaluminum reagent; Organosilicon reagent; Thymidine

Indexed keywords

4' BENZENESULFONYL; ALUMINUM DERIVATIVE; BENZENE DERIVATIVE; NUCLEOPHILE; ORGANOSILICON DERIVATIVE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67649342178     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.078     Document Type: Article
Times cited : (12)

References (29)
  • 9
    • 33744525735 scopus 로고    scopus 로고
    • Data taken from. Dean J.H. (Ed), McGraw-Hill, New York, NY
    • Data taken from. In: Dean J.H. (Ed). Lange's Handbook of Chemistry. 15th ed. (1999), McGraw-Hill, New York, NY
    • (1999) Lange's Handbook of Chemistry. 15th ed.
  • 10
    • 67649323155 scopus 로고    scopus 로고
    • For typical examples, see
    • For typical examples, see:
  • 17
    • 67649357724 scopus 로고    scopus 로고
    • note
    • 3N in this reaction lowered the yield of 6 to 32%.
  • 19
    • 67649330248 scopus 로고    scopus 로고
    • note
    • Of the two protons at the 5′-position, the one that appears at a lower field is designated as H-5′b, and the other as H-5′a, throughout the text and the Experimental section. The same applies to the two protons at the 2′-position.
  • 20
    • 67649330247 scopus 로고    scopus 로고
    • note
    • 3).
  • 21
    • 33644924640 scopus 로고
    • 3) δ 43.95, 123.47, 129.34, 131.01, 145.69. These data are identical with those of commercially available sample (purchased from Aldrich). Reaction of benzenesulfonyl chlorides with trialkylaluminums has been reported to yield alkyl aryl sulfoxide:
    • 3) δ 43.95, 123.47, 129.34, 131.01, 145.69. These data are identical with those of commercially available sample (purchased from Aldrich). Reaction of benzenesulfonyl chlorides with trialkylaluminums has been reported to yield alkyl aryl sulfoxide:. Jahnke D., and Reinheckel H. Organomet. Chem. Syn. (1970/1971) 31
    • (1970) Organomet. Chem. Syn. , pp. 31
    • Jahnke, D.1    Reinheckel, H.2
  • 23
    • 67649314637 scopus 로고    scopus 로고
    • note
    • Partial 5′-O-desilylation of 18α to yield 6 was the sole event observed.
  • 24
    • 67649314636 scopus 로고    scopus 로고
    • note
    • 5SSi: C, 56.87; H, 6.94; N, 6.03. Found: C, 56.97; H, 7.07; N, 5.88.
  • 25
    • 67649377207 scopus 로고    scopus 로고
    • note
    • 1H NMR measurement of a mixture of 22β, 22α, 20β, and 21β by integrating the respective H-6 resonance.
  • 26
    • 67649374471 scopus 로고    scopus 로고
    • note
    • 3SiC{triple bond, long}CAl(Et)Cl, the reagent used in our previous study in Ref. 6, the α-l-nucleoside 22α was formed as the sole product in 58% yield, presumably through chlorination at the 4′-position.
  • 27
    • 67649330246 scopus 로고    scopus 로고
    • note
    • 3 with a THF solution of PhMgBr as described in the Experimental section.
  • 28
    • 67649370082 scopus 로고    scopus 로고
    • note
    • 2AlCN in toluene at rt for 16 h.
  • 29
    • 67649323154 scopus 로고    scopus 로고
    • note
    • ++H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.