Glycosidation Promoted by a Reusable Solid Superacid in Supercritical Carbon Dioxide

✍ Scribed by Xue-Bing Li; Masato Ogawa; Toshiki Monden; Takahiro Maeda; Eri Yamashita; Mariko Naka; Masao Matsuda; Hiroshi Hinou; Shin-Ichiro Nishimura

• Book ID: 101566194
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 175 KB
• Volume: 45
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200602161

✦ Synopsis

Functional roles of glycoconjugates are of growing importance owing to carbohydrate-mediated signal transductions, which are crucial steps for a variety of biological phenomena such as cellular differentiation, aging, immune systems, infections, and malignant alterations of cells. Synthetic studies of carbohydrates are indispensable both for elucidating essential structures of the functional glycoconjugates and for producing therapeutic reagents of carbohydrate-related diseases. [1] Glycosidation is one of the most important reactions in chemical synthesis of glycoconjugates. [2] In recent years, although there has been an increasing interest in environmentally more-sustainable chemical processes, [3] a practical and cleaner chemical synthetic process of carbohydrates has been discussed very little except for a few pioneering efforts. [4] The advent of a highly efficient, safe, and environmentally benign method for the glycosidation is strongly expected because this key technology will allow for practical and industrial scale production of natural and unnatural glycosides. Enzyme-assisted synthesis has been recognized to be a much more sustainable and efficient strategy than pure chemical protocols in terms of the construction of various seeds libraries for the discovery and research of therapeutic reagents. [5] However, the present potentials are not high enough for large scale synthesis of drug candidates required for the following clinical trials.