α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units

• Published in: Bioorganic & medicinal chemistry letters Vol. 13; no. 6; pp. 1063 - 1066
• Main Authors: Matsuda, Hiroko, Ohara, Keiichiro, Morii, Yasuharu, Hashimoto, Masaru, Miyairi, Kazuo, Okuno, Toshikatsu
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 24.03.2003; Elsevier
• Subjects: Carbohydrate Sequence; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Glucose - analogs & derivatives; Glucose - chemistry; Glycosylation; Indicators and Reagents; Models, Molecular; Molecular Mimicry; Molecular Sequence Data; Monosaccharides - chemistry; Oligosaccharides - chemistry; Organic chemistry; Preparations and properties; Sulfur heterocycle; Deprotection; Thioglycoside; Glycoside; Glycosylation; Selectivity; Chemical synthesis; Tetrasaccharide
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(03)00072-6

A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. A isomaltotetraoside analogue was synthesized as the application.