title: Phthalic Anhydride-Mediated Direct Glycosylation of Anomeric Hydroxy Arabinofuranose: Synthesis of Repeating Oligoarabinofuranoside and Tetradecasaccharide Arabinan Motif of Mycobacterial Cell Wall.
abstract: An efficient direct phthalic anhydride-mediated one-pot glycosylation method employing anomeric hydroxy arabinofuranose as glycosyl donor and triflic anhydride as activating agent has been developed. This method afforded the desired di- and oligoarabinofuranosides in good yields even in gram scale glycosylation when t-butylphthalic anhydride was used. Moreover, our new method can be further extended to the syntheses of repeating oligoarabinofuranoside and tetradecasaccharide arabinan motif found in mycobacterial cell wall.
authors.affiliation: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University , Seoul 120-749, Korea.
authors.forename: Bo-Young
authors.initials: BY
authors.lastname: Lee
authors.affiliation: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University , Seoul 120-749, Korea.
authors.forename: Jung Woo
authors.initials: JW
authors.lastname: Oh
authors.affiliation: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University , Seoul 120-749, Korea.
authors.forename: Ju Yuel
authors.initials: JY
authors.lastname: Baek
authors.affiliation: Department of Chemistry, Kwangwoon University , Seoul 139-701, Korea.
authors.forename: Heung Bae
authors.initials: HB
authors.lastname: Jeon
authors.affiliation: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University , Seoul 120-749, Korea.
authors.forename: Kwan Soo
authors.initials: KS
authors.lastname: Kim
mesh_terms: D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002473:Cell Wall / Q000737:chemistry*; D006031:Glycosylation; D009161:Mycobacterium / Q000737:chemistry*; D010796:Phthalic Anhydrides / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D010796:Phthalic Anhydrides; D011134:Polysaccharides; C431714:arabinofuranose; C030080:araban; D001089:Arabinose; C043103:phthalic anhydride