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Volumn 33, Issue 13, 1994, Pages 1383-1386

Samarium Iodide Induced Intramolecular C‐Glycoside Formation: Efficient Radical Formation in the Absence of an Additive

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EID: 33748227304     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199413831     Document Type: Article
Times cited : (98)

References (36)
  • 4
    • 84989526607 scopus 로고
    • An application of this approach using a 9‐endo cyclization mode for the expedient construction of two C‐disaccharides has just been described, although with the large ring size used, α‐C‐glycosides are predominantly obtained due to the anomeric effect:, J. Chem. Soc. Chem. Commun., 864–865
    • (1993)
    • Xin, Y.C.1    Mallet, J.‐M.2    Sinaÿ, P.3
  • 6
    • 84989595146 scopus 로고    scopus 로고
    • For examples of the construction of C‐glycosides by intermolecular or nonsilicon‐tethered intramolecular reactions of anomeric radicals see ref. [1].
  • 32
    • 84989511575 scopus 로고    scopus 로고
    • The 2‐pyridylsulfonyl glycosides were easily prepared as previously described for the phenyl sulfones (see ref. [9]). Attempts to prepare the corresponding imidazolyl sulfones were problematic and interestingly, the free C2 hydroxyl group failed to be silylated.
  • 33
    • 0024826444 scopus 로고
    • The procedure reported by Stork and Keitz led to low or no yields of silylated products. In the case of a nonvolatile alkyne, the excess could easily be recovered by desilylation of the major by‐product, the dialkynyldimethylsilane. Attempts to prepare an alternative and more efficient silylation method is underway in our laboratory
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6981-6984
    • Stork, G.1    Keitz, P.2
  • 34
    • 84989523174 scopus 로고    scopus 로고
    • 3O), 3.78 (m, 1H, H‐5), 3.80 (ddd, 1H, J = 9.2, 5.3, 2.6 Hz, H‐5′), 4.02 (dd, 1H, J = 12.3, 2.6 Hz, H‐6a′), 4.15 (ddd, 1H, J = 12.2, 6.0, 3.5 Hz, H‐l′), 4.24 (dd, 1H, J = 12.3, 5.3 Hz, H‐6b′), 4.84 (dd, 1H, J = 10.2, 3.7 Hz, H‐2), 4.85 (dd, 1H, J = 9.8, 9.8 Hz, H‐4), 4.91 (d, 1H, J = 3.7 Hz, H‐l), 4.97 (dd, 1H, J = 9.2, 9.2 Hz, H‐4′), 5.07 (dd, 1H, J = 9.9, 6.0 Hz, H‐2′), 5.32 (dd, 1H, J = 9.9, 9.2 Hz, H‐3′), 5.44 (dd, 1H, J = 10.2, 9.8 Hz, H‐3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.