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Volumn 61, Issue 18, 1996, Pages 6189-6198

Chemistry of 1-alkoxy-1-glycosyl radicals: Formation of β-mannopyranosides by radical decarboxylation and decarbonylation of manno-heptulosonic acid glycoside derivatives

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

EID: 0029834481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960799q     Document Type: Article
Times cited : (39)

References (75)
  • 1
    • 16044375035 scopus 로고    scopus 로고
    • note
    • (a) For a compilation of references to recent advances in this area, see footnote 2b.
  • 7
    • 33847798596 scopus 로고
    • Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
    • (1976) J. Org. Chem. , vol.41 , pp. 2222
    • Hayday, K.1    McKelvey, R.D.2
  • 8
    • 0000516387 scopus 로고
    • Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 615
    • Beckwith, A.L.J.1    Easton, C.J.2
  • 9
    • 37049080023 scopus 로고
    • Axial quenching of 1-alkoxy-1-glycosyl radicals was initially predictable in so far as it is effectively the microscopic reverse of hydrogen atom abstraction from alkoxytetrahydropyrans by electrophilic radicals wherein the axial hydrogen is abstracted up to eight times as rapidly as the equatorial one: (a) Hayday, K.; McKelvey, R. D. J. Org. Chem. 1976, 41, 2222. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615. (c) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
    • (1987) J. Chem. Soc., Perkin Trans. 2 , pp. 1801
    • Beckwith, A.L.J.1    Brumby, S.2
  • 40
    • 0345529661 scopus 로고
    • For previous examples of the oxidation of substituted furans to 1,2-dicarbonyl compounds, see: (a) White, H. M.; Colomb, H. O.; Bailey, P. S. J. Org. Chem. 1965, 30, 481. (b) Bailey, P. S.; White, H. M.; Colomb, H. O. J. Org. Chem. 1965, 30, 487.
    • (1965) J. Org. Chem. , vol.30 , pp. 481
    • White, H.M.1    Colomb, H.O.2    Bailey, P.S.3
  • 41
    • 16044373991 scopus 로고
    • For previous examples of the oxidation of substituted furans to 1,2-dicarbonyl compounds, see: (a) White, H. M.; Colomb, H. O.; Bailey, P. S. J. Org. Chem. 1965, 30, 481. (b) Bailey, P. S.; White, H. M.; Colomb, H. O. J. Org. Chem. 1965, 30, 487.
    • (1965) J. Org. Chem. , vol.30 , pp. 487
    • Bailey, P.S.1    White, H.M.2    Colomb, H.O.3
  • 49
    • 16044366551 scopus 로고    scopus 로고
    • note
    • Interestingly, this strain is mainly due to the 4,6-, rather than the 2,3-acetonide, as subsequent experiments with 4,6-O-isopropylidene-2,3-di-O-[[2-(trimethylsilyl)ethoxy]methyI]mannonolactone gave exactly analogous results.
  • 51
    • 0003405157 scopus 로고
    • Georg Thieme Verlag: Stuttgart
    • Reviews: (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; Wiley, New York, 1991. (b) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, 1994.
    • (1994) Protecting Groups
    • Kocienski, P.J.1
  • 67
    • 0026500414 scopus 로고
    • Attempted application of this exchange process to the glycosyl donor 28 failed, probably due to poisoning of the catalysts by the thiol ether moiety: Yin, H.; Franck. R. W.; Cheng, S.-L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
    • (1992) J. Org. Chem. , vol.57 , pp. 644
    • Yin, H.1    Franck, R.W.2    Cheng, S.-L.3    Quigley, G.J.4    Todaro, L.5
  • 72
    • 16044365256 scopus 로고    scopus 로고
    • note
    • Owing to insufficient spectral resolution, it is unclear whether this isomer differs from 4 in anomeric configuration or is the result of a manno- to gluco-isomerization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.