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Volumn 5, Issue 20, 2003, Pages 3763-3766

Stereodirected synthesis of aryl α-C-glycosides from 2-O-arylsilyl-glucopyranosides

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; GLUCOPYRANOSIDE; GLYCOSIDE; ORGANOSILICON DERIVATIVE; PYRAN DERIVATIVE;

EID: 0142011100     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035529q     Document Type: Article
Times cited : (23)

References (27)
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    • Epiorientin: Bhatia, V. K.; Seshadri, T. R. Phytochemistry 1967, 6, 1033-1034. Parkinsonin B: Bhatia, V. K.; Gupta, S. R.; Seshadri, T. R. Tetrahedon 1966, 22, 1147-1152. However, the structure of these compounds appears to be erroneous; see: Besson, E.; Chopin, J.; Gunasegaran, R.; Nair, A. G. R. Phytochemistry 1980, 19, 2787-2788. See also: Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Carbohydr. Res. 2001, 334, 183-193.
    • (1967) Phytochemistry , vol.6 , pp. 1033-1034
    • Bhatia, V.K.1    Seshadri, T.R.2
  • 5
    • 0004359302 scopus 로고
    • Epiorientin: Bhatia, V. K.; Seshadri, T. R. Phytochemistry 1967, 6, 1033-1034. Parkinsonin B: Bhatia, V. K.; Gupta, S. R.; Seshadri, T. R. Tetrahedon 1966, 22, 1147-1152. However, the structure of these compounds appears to be erroneous; see: Besson, E.; Chopin, J.; Gunasegaran, R.; Nair, A. G. R. Phytochemistry 1980, 19, 2787-2788. See also: Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Carbohydr. Res. 2001, 334, 183-193.
    • (1966) Tetrahedon , vol.22 , pp. 1147-1152
    • Bhatia, V.K.1    Gupta, S.R.2    Seshadri, T.R.3
  • 6
    • 0004282354 scopus 로고
    • Epiorientin: Bhatia, V. K.; Seshadri, T. R. Phytochemistry 1967, 6, 1033-1034. Parkinsonin B: Bhatia, V. K.; Gupta, S. R.; Seshadri, T. R. Tetrahedon 1966, 22, 1147-1152. However, the structure of these compounds appears to be erroneous; see: Besson, E.; Chopin, J.; Gunasegaran, R.; Nair, A. G. R. Phytochemistry 1980, 19, 2787-2788. See also: Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Carbohydr. Res. 2001, 334, 183-193.
    • (1980) Phytochemistry , vol.19 , pp. 2787-2788
    • Besson, E.1    Chopin, J.2    Gunasegaran, R.3    Nair, A.G.R.4
  • 7
    • 0035975199 scopus 로고    scopus 로고
    • Epiorientin: Bhatia, V. K.; Seshadri, T. R. Phytochemistry 1967, 6, 1033-1034. Parkinsonin B: Bhatia, V. K.; Gupta, S. R.; Seshadri, T. R. Tetrahedon 1966, 22, 1147-1152. However, the structure of these compounds appears to be erroneous; see: Besson, E.; Chopin, J.; Gunasegaran, R.; Nair, A. G. R. Phytochemistry 1980, 19, 2787-2788. See also: Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Carbohydr. Res. 2001, 334, 183-193.
    • (2001) Carbohydr. Res. , vol.334 , pp. 183-193
    • Kumazawa, T.1    Kimura, T.2    Matsuba, S.3    Sato, S.4    Onodera, J.5
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    • See the following for selected examples. Pyridyl thioglycosides with dimethoxybenzene: Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296. Trichloroacetimidates with furans: Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831. Trifluoroacetates with bis(TMS)resorcinol: Cai, M. S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129. See ref 6 for the α/β ratio in several C-arylation processes.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4289-4296
    • Stewart, A.O.1    Williams, R.M.2
  • 14
    • 84985257131 scopus 로고
    • See the following for selected examples. Pyridyl thioglycosides with dimethoxybenzene: Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296. Trichloroacetimidates with furans: Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831. Trifluoroacetates with bis(TMS)resorcinol: Cai, M. S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129. See ref 6 for the α/β ratio in several C-arylation processes.
    • (1987) Liebigs Ann. Chem. , pp. 825-831
    • Schmidt, R.R.1    Effenberger, G.2
  • 15
    • 0000662481 scopus 로고
    • See ref 6 for the α/β ratio in several C-arylation processes
    • See the following for selected examples. Pyridyl thioglycosides with dimethoxybenzene: Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296. Trichloroacetimidates with furans: Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831. Trifluoroacetates with bis(TMS)resorcinol: Cai, M. S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129. See ref 6 for the α/β ratio in several C-arylation processes.
    • (1989) Carbohydr. Res. , vol.191 , pp. 125-129
    • Cai, M.S.1    Qiu, D.-X.2
  • 18
    • 0342936076 scopus 로고    scopus 로고
    • O-Glycoside formation by IAD: Jung, K.-H.; Müller, M.; Schmidt, R. R. Chem. Rev. 2000, 100, 4423-4442. C-Glycoside formation by IAD via silicon tether: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
    • (2000) Chem. Rev. , vol.100 , pp. 4423-4442
    • Jung, K.-H.1    Müller, M.2    Schmidt, R.R.3
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    • O-Glycoside formation by IAD: Jung, K.-H.; Müller, M.; Schmidt, R. R. Chem. Rev. 2000, 100, 4423-4442. C-Glycoside formation by IAD via silicon tether: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
    • (1995) Chem. Rev. , vol.95 , pp. 1253-1277
    • Bols, M.1    Skrydstrup, T.2
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    • note
    • The nature of the silylated species formed in the reaction and isolated before treatment with TBAF could not be identified.
  • 25
    • 0142100285 scopus 로고    scopus 로고
    • note
    • 4NF (90 mg, 2 equiv) was added to a solution of the residue in THF (15 mL) at 0°C. After 2 h, the solvent was removed in vacuo. Flash chromatography (silica gel, eluent petroleum ether/AcOEt 7:1) provided the desired product 8 (69 mg, 74%).
  • 26
    • 0142131966 scopus 로고    scopus 로고
    • note
    • Ar-OMe), 169.09, 169.29, 169.82, 170.03 (C=O).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.