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Volumn 75, Issue 19, 2010, Pages 6402-6410

Toward l-homo-DNA: Stereoselective de novo synthesis of β-L-erythro-hexopyranosyl nucleosides

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIZATION; DE NOVO SYNTHESIS; DOMINO REACTIONS; ENANTIOPURE; ERYTHRO; GLYCOSIDATIONS; IN-SITU; NOVEL ROUTE; NUCLEOBASES; STEREO-SELECTIVE; SUGAR MOIETY; TRANSFER MECHANISMS;

EID: 77957167369     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100691y     Document Type: Article
Times cited : (25)

References (57)
  • 35
    • 84890766709 scopus 로고    scopus 로고
    • Tietze L.F. Brasche G. Gericke K.M. See:;;;, Eds.; Wiley-VCH: Weinheim, Germany.
    • See: Domino Reactions in Organic Synthesis; Tietze, L. F.; Brasche, G.; Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
    • (2006) Domino Reactions in Organic Synthesis
  • 37
    • 1642370024 scopus 로고    scopus 로고
    • Fraser-Reid B.O. Tatsuta K. Thiem J. In;;;, Eds.; Springer: Berlin, Germany,; Chapter 3.6
    • Sekine, M. In Glycoscience; Fraser-Reid, B. O.; Tatsuta, K.; Thiem, J., Eds.; Springer: Berlin, Germany, 2001; Chapter 3.6, pp 673 - 689.
    • (2001) Glycoscience , pp. 673-689
    • Sekine, M.1
  • 42
    • 77957172127 scopus 로고    scopus 로고
    • Moreover, even though cyclonucleosides 14, 15, and 16 differ in the nature of the protective groups at the C -3′/ C -4′ positions and in the configuration of the stereogenic centers, it was calculated that these structural differences did not significantly influence reactivity of the resulting nucleosides (data not shown)
    • Moreover, even though cyclonucleosides 14, 15, and 16 differ in the nature of the protective groups at the C -3′/ C -4′ positions and in the configuration of the stereogenic centers, it was calculated that these structural differences did not significantly influence reactivity of the resulting nucleosides (data not shown).
  • 43
    • 77957126697 scopus 로고    scopus 로고
    • See the Supporting Information.
    • See the Supporting Information.
  • 52
    • 0026671478 scopus 로고
    • For an application of glycosyl sulfoxides in N -glycosidation reactions, see
    • For an application of glycosyl sulfoxides in N -glycosidation reactions, see: Chanteloup, L.; Beau, J.-M. Tetrahedron Lett. 1992, 33, 5347
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5347
    • Chanteloup, L.1    Beau, J.-M.2
  • 53
    • 77957146984 scopus 로고    scopus 로고
    • 2O gave similar results.
    • 2O gave similar results.
  • 55
    • 0031749791 scopus 로고    scopus 로고
    • The authors did not further investigate into the reaction mechanism of the sulfoxide glycosidation at low temperatures, for example, analyzing the formation of the glycosyl sulfenate intermediates (see for example:;;), as the low yield achieved under the best stereoselective conditions (entry 5)'does not render the reaction of practical interest for our synthetic purposes
    • The authors did not further investigate into the reaction mechanism of the sulfoxide glycosidation at low temperatures, for example, analyzing the formation of the glycosyl sulfenate intermediates (see for example: Gildersleeve, J.; Pascal, R. A., Jr.; Kahne, D. J. Am. Chem. Soc. 1998, 120, 5961-5969), as the low yield achieved under the best stereoselective conditions (entry 5) does not render the reaction of practical interest for our synthetic purposes
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5961-5969
    • Gildersleeve, J.1    Pascal Jr., R.A.2    Kahne, D.3
  • 56
    • 77957152234 scopus 로고    scopus 로고
    • Reaction with the pure 9β gave nearly the same results.
    • Reaction with the pure 9β gave nearly the same results.
  • 57
    • 0028006129 scopus 로고
    • This reaction augments previous results carried out on similar substrates:;;;;;, and references cited therein
    • This reaction augments previous results carried out on similar substrates: Augustyns, K.; Rozenski, J.; Van Aerschot, A.; Busson, R.; Claes, P.; Herdewijn, P. Tetrahedron 1994, 50, 1189-1198 and references cited therein
    • (1994) Tetrahedron , vol.50 , pp. 1189-1198
    • Augustyns, K.1    Rozenski, J.2    Van Aerschot, A.3    Busson, R.4    Claes, P.5    Herdewijn, P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.