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Volumn 54, Issue 50, 2013, Pages 6889-6891

Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates

Author keywords

Carbohydrates; Deoxysugars; Glycosides; Natural products; Suzuki Miyaura

Indexed keywords

6 DEOXY 3,4 DI O BENZYL LEVO RHAMNAL; AROMATIC COMPOUND; C ARYLGLYCAL DERIVATIVE; CHEMICAL COMPOUND; DIHYDROPYRANYLPHOSPHATE DERIVATIVE; ESTER DERIVATIVE; GLYCOSIDE; KETENE ACETAL PHOSPHATE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84893911653     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.031     Document Type: Article
Times cited : (15)

References (79)
  • 20
    • 0001397662 scopus 로고
    • For selected references on C-glycoside synthesis:
    • For selected references on C-glycoside synthesis:Matsumoto, T., Katsuki, M., Suzuki, K., Tetrahedron Lett., 29, 1988, 6935.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6935
    • Matsumoto, T.1    Katsuki, M.2    Suzuki, K.3
  • 47
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    • Metal-Catalyzed Cross-Coupling Reactions
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    • Metal-Catalyzed Cross-Coupling Reactions. Diederich, F., Meijere, A., (eds.), 2004, Wiley-VCH, Weinheim.
    • (2004)
    • Diederich, F.1    Meijere, A.2
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    • Topics in Current Chemistry
    • Springer-Verlag New York
    • Topics in Current Chemistry. Miyaura, N., (eds.), Vol. 219, 2002, Springer-Verlag, New York.
    • (2002) , vol.219
    • Miyaura, N.1
  • 58
    • 0032577032 scopus 로고    scopus 로고
    • A similar effect, using Hünig's base, has been reported in Stille cross-coupling reactions:
    • A similar effect, using Hünig's base, has been reported in Stille cross-coupling reactions:Smith, A.B. III, Ott, G.R., J. Am. Chem. Soc., 120, 1998, 3935.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3935
    • Smith, A.B.1    Ott, G.R.2
  • 59
    • 85063939895 scopus 로고    scopus 로고
    • The involvement of arylboronate esters rather than arylboronic acids (Ref. 8a) as the coupling partner resulted in substantially improved yields in a number of cases. Additionally, the current method has also allowed for an expansion of substrate scope as C-arylglycals that were previously inaccessible using arylboronic acids (5c, 5e, 5f, 5k, 5m) are efficiently produced employing arylboronate esters. Most importantly, the use of arylboronic acids failed to produce any C-arylglycals when carbohydrate-derived ketene acetal phosphate 10 was employed under a variety of reaction conditions.
    • The involvement of arylboronate esters rather than arylboronic acids (Ref. 8a) as the coupling partner resulted in substantially improved yields in a number of cases. Additionally, the current method has also allowed for an expansion of substrate scope as C-arylglycals that were previously inaccessible using arylboronic acids (5c, 5e, 5f, 5k, 5m) are efficiently produced employing arylboronate esters. Most importantly, the use of arylboronic acids failed to produce any C-arylglycals when carbohydrate-derived ketene acetal phosphate 10 was employed under a variety of reaction conditions.
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    • Antitumor antibiotics of the aureolic acid group: chromomycin A3, mithramycin A, and olivomycin A
    • A. Aszalos CRC Press Boca Raton, FL
    • Skarbek, J.D., Speedie, M.K., Antitumor antibiotics of the aureolic acid group: chromomycin A3, mithramycin A, and olivomycin A. Aszalos, A., (eds.) Antitumor Compounds of Natural Origin, Vol. 1, 1981, CRC Press, Boca Raton, FL, 191.
    • (1981) Antitumor Compounds of Natural Origin , vol.1 , pp. 191
    • Skarbek, J.D.1    Speedie, M.K.2
  • 78
    • 0000677383 scopus 로고    scopus 로고
    • A similar hypothesis was made in the application of the Takai olefination procedure for the preparation of acyclic enol ethers:
    • A similar hypothesis was made in the application of the Takai olefination procedure for the preparation of acyclic enol ethers:Ranier, J.D., Allwein, S.P., J. Org. Chem., 63, 1998, 5310.
    • (1998) J. Org. Chem. , vol.63 , pp. 5310
    • Ranier, J.D.1    Allwein, S.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.