Indirect synthetic route to α-l-fucosides via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation. Issue 26 (23rd June 2020)

• Record Type: Journal Article
• Authors: Tomida, Hirotaka; Matsuhashi, Takuya; Tanaka, Hide-Nori; Komura, Naoko; Ando, Hiromune; Imamura, Akihiro; Ishida, Hideharu
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 26(2020)
• Page Start: 5017
• Page End: 5033
• Publication Date: 2020-06-23
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01128b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The indirect synthetic method for α-l -fucosides has been developed and its broad applicability to naturally occurring α-l -fucosides has been demonstrated. Abstract : We developed an indirect synthetic method for α-l -fucosides. Based on the fact that l -fucose is 6-deoxy-l -galactose, our strategy consists of the stereoselective construction of α-l -galactoside and its conversion to α-l -fucoside via C6-deoxygenation. The formation of α-l -galactoside is strongly directed using 4, 6- O -di- tert -butylsilylene(DTBS)-protected l -galactosyl donors. The DTBS-directed α-l -galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-l -galactosides, the Barton–McCombie reaction facilitated the conversion to l -fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-l -fucosides.