Improved and large-scale synthesis of different protected d-glucuronals

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• 作者：Hannes Mikula ; ^{hannes.mikula@tuwien.ac.at} ; Dominik Matscheko ; Markus Schwarz ; Christian Hametner ; Johannes Frö ; hlich
• 关键词：d-Glucuronals ; protected ; Large-scale synthesis ; Methyl 3 ; 4-di-O-acetyl-d-glucuronal ; Benzyl 3 ; 4-di-O-benzyl-d-glucuronal ; d-Glucuronal ; silyl protected ; TEMPO/BAIB-mediated oxidation
• 刊名：Carbohydrate Research
• 出版年：2013
• 出版时间：5 April, 2013
• 年：2013
• 卷：370
• 期：Complete
• 页码：19-23
• 全文大小：426 K

文摘

Although different protected d-glucuronals are used as precursors for the preparation of many compounds, standard procedures and large-scale syntheses are still not described in the literature. In the course of the development of different protected d-glucuronyl donors we developed several versatile methods that can be used for fast and reproducible preparation of large amounts of the key intermediates. d-Glucuronolactone was converted to methyl 3,4-di-O-acetyl-d-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-d-glucal was used as starting material for an improved preparation of benzyl protected d-glucuronal, which significantly accelerates and simplifies similar methods described in the literature.