title: Synthesis of 3-aminopropyl glycosides of linear β-(1 → 3)-D-glucooligosaccharides.
abstract: 3-Aminopropyl glycosides of a series of linear β-(1 → 3)-linked D-glucooligosaccharides containing from 3 to 13 monosaccharide units were efficiently prepared. The synthetic scheme featured highly regioselective glycosylation of 4,6-O-benzylidene-protected 2,3-diol glycosyl acceptors with a disaccharide thioglycoside donor bearing chloroacetyl groups at O-2' and -3' as a temporary protection of the diol system. Iteration of the deprotection and glycosylation steps afforded the series of the title oligoglucosides differing in length by two monosaccharide units. A novel procedure for selective removal of acetyl groups in the presence of benzoyl ones consisting in a brief treatment with a large excess of hydrazine hydrate has been proposed.
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia.
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Yashunsky
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia.
authors.forename: Yury E
authors.initials: YE
authors.lastname: Tsvetkov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia.
authors.forename: Alexey A
authors.initials: AA
authors.lastname: Grachev
authors.affiliation: Division of Structural Studies, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia.
authors.forename: Alexander O
authors.initials: AO
authors.lastname: Chizhov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia. Electronic address: nen@ioc.ac.ru.
authors.forename: Nikolay E
authors.initials: NE
authors.lastname: Nifantiev
mesh_terms: D060326:Chemistry Techniques, Synthetic; D005947:Glucose / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D009844:Oligosaccharides / Q000737:chemistry*
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; D005947:Glucose
keywords: De-O-acetylation; β-(1→3)-Glucooligosaccharides; β-Glucan