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Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 205-215

http://dx.doi.org/10.1351/PAC-CON-08-09-14

A strategy for constructing C-sialosides based on Ireland-Claisen rearrangement and its application for synthesis of CF2-linked ganglioside GM4 analog

Mikiko Sodeoka1, Go Hirai1, Toru Watanabe1 and Taeko Miyagi2

1 Synthetic Organic Chemistry Laboratory, RIKEN, Hirosawa, Wako, Saitama 351 0198, Japan
2 Division of Biochemistry, Miyagi Cancer Center Research Institute, Natori 981-1293, Japan, and CREST,JST Kawaguchi 332-1102, Japan

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  • Leclerc Eric, Pannecoucke Xavier, Ethève-Quelquejeu Mélanie, Sollogoub Matthieu: Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics. Chem. Soc. Rev. 2013, 42, 4270. <http://dx.doi.org/10.1039/c2cs35403a>
  • Kato Marie, Hirai Go, Sodeoka Mikiko: Studies on the Selectivity between Glycosylation and Intermolecular Aglycone Transfer of Thioglucoside in Synthesis of Lactose Derivatives. Chem Lett (Japan) 2011, 40, 877. <http://dx.doi.org/10.1246/cl.2011.877>
  • Sodeoka Mikiko, Hirai Go, Watanabe Toru, Miyagi Taeko: ChemInform Abstract: A Strategy for Constructing C-Sialosides Based on Ireland-Claisen Rearrangement and Application for the Synthesis of a CF2-Linked Ganglioside GM4 Analogue. ChemInform 2009, 40. <http://dx.doi.org/10.1002/chin.200931238>