Synthesis of 4′- O-acetyl-maltose and α- d-galactopyranosyl-(1→4)- d-glucopyranose for biochemical studies of amylose biosynthesis

• Published in: Carbohydrate research Vol. 330; no. 3; pp. 309 - 318
• Main Authors: Motawia, Mohammed Saddik, Olsen, Carl Erik, Denyer, Kay, Smith, Alison M., Møller, Birger Lindberg
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.02.2001; Elsevier
• Subjects: Amylose - biosynthesis; Amylose - chemistry; Biochemistry & Molecular Biology; Carbohydrate Conformation; Chemistry; Chemistry, Applied; Chemistry, Organic; Disaccharides - chemical synthesis; Disaccharides - chemistry; Glycosidation; Glycosyl trichloroacetamidate; Hydrogenolysis; Indicators and Reagents; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Maltose - analogs & derivatives; Maltose - chemical synthesis; Maltose - chemistry; Maltose derivatives; Models, Molecular; Phenyl thioglycosides; Physical Sciences; Science & Technology; Structure-Activity Relationship; α- d-Galactopyranosyl-(1→4)- d-glucopyranose; Maltose derivatives; Glycosyl trichloroacetamidate; Phenyl thioglycosides; Glycosidation; Hydrogenolysis; α- d-Galactopyranosyl-(1→4)- d-glucopyranose; STARCH GRANULES; OLIGOSACCHARIDES; AMYLOPECTIN; glycosyl trichloroacetamidate; alpha-D-galactopyranosyl-(1 -> 4)-D-glucopyranose; phenyl thioglycosides; glycosidation; maltose derivatives; hydrogenolysis
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(00)00306-2

The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4′-OH group or by reversing its configuration, is reported. For synthesis of the 4′- O-acetylated analog, β-maltose was converted into its per- O-benzylated-4′,6′- O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6′. Acetylation at C-4′ of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra- O-benzyl-α/β- d-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-tri- O-benzyl-1-thio-β- d-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog.