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Volumn 39, Issue 35, 1998, Pages 6299-6302

Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIDEOXYRIBOFURANOSE; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

EID: 0032572874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01335-5     Document Type: Article
Times cited : (18)

References (27)
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    • 5. For reviews of N-glycosylations: Wilson, L. J.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465. N-Glycosylation reactions of glycosyl donors of type 3 with a modest diastereoselectivity were briefly reported: Lau, W. Y.; Zhang, L.; Cheng, D.; Wang, J.; Zhao, K. Thetrahedron Lett. 1996, 37, 4297.
    • (1995) Synthesis , pp. 1465
    • Wilson, L.J.1    Hager, M.W.2    El-Kattan, Y.A.3    Liotta, D.C.4
  • 17
    • 0029975339 scopus 로고    scopus 로고
    • 5. For reviews of N-glycosylations: Wilson, L. J.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465. N-Glycosylation reactions of glycosyl donors of type 3 with a modest diastereoselectivity were briefly reported: Lau, W. Y.; Zhang, L.; Cheng, D.; Wang, J.; Zhao, K. Thetrahedron Lett. 1996, 37, 4297.
    • (1996) Thetrahedron Lett. , vol.37 , pp. 4297
    • Lau, W.Y.1    Zhang, L.2    Cheng, D.3    Wang, J.4    Zhao, K.5
  • 19
    • 0000230270 scopus 로고
    • 6. Vorbrüggen, H.; Kroilkiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234. Vorbrüggen. H. Acc. Chem. Res. 1995, 28, 509.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 509
    • Vorbrüggen, H.1
  • 20
    • 0010502662 scopus 로고    scopus 로고
    • note
    • 31P-NMR, IR and MS analyses.
  • 21
    • 0010527917 scopus 로고    scopus 로고
    • note
    • 3); relatively strong correlations between the protons on benzoyl and the l-ethoxy functional groups were observed with 10a,b.
  • 22
    • 0010502061 scopus 로고    scopus 로고
    • note
    • 9. The benzoyl protecting group of 8a,b was found to be a good directing functionality to induce complete diastereoselectivity (>99% de) under the conditions. See ref. 4a for a comparison.
  • 23
    • 0025817098 scopus 로고
    • 10. Recent examples for neighboring group participation of the thiocarbonyl functionality at the 3-position: (a) Lavallee, J.-F.; Just, G. Tetrahedron Lett. 1991, 32, 3469.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3469
    • Lavallee, J.-F.1    Just, G.2
  • 26
    • 0010502062 scopus 로고    scopus 로고
    • note
    • 11. The bond lengths are based on MM 2 calculation with CAChe Worksystem (SONY/Tektronix Corporation).
  • 27
    • 0010500116 scopus 로고    scopus 로고
    • note
    • ++thy).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.