Boronic Acid-Catalyzed Regioselective Koenigs–Knorr-Type Glycosylation

• Published in: Journal of organic chemistry Vol. 86; no. 8; pp. 5973 - 5982
• Main Authors: Shimada, Naoyuki, Sugimoto, Tomoya, Noguchi, Mao, Ohira, Chikako, Kuwashima, Yutaro, Takahashi, Naoya, Sato, Noriko, Makino, Kazuishi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.04.2021; Amer Chemical Soc
• Subjects: boronic acids; catalysts; Chemistry; Chemistry, Organic; glycols; glycosidic linkages; glycosylation; organic chemistry; Physical Sciences; regioselectivity; Science & Technology; silver oxide; TRANSIENT MASKING; ACTIVATION; OLIGOSACCHARIDES; ACYLATION; NATURAL-PRODUCTS; ALKYLATION; HEXOPYRANOSIDE; GLYCOSIDATIONS; SILYLATION; CARBOHYDRATE-CHEMISTRY

Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proce...