title: Improved and large-scale synthesis of different protected D-glucuronals.
abstract: 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.
authors: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna 1060, Austria. hannes.mikula@tuwien.ac.at
authors: Hannes
authors: H
authors: Mikula
authors: Dominik
authors: D
authors: Matscheko
authors: Markus
authors: M
authors: Schwarz
authors: Christian
authors: C
authors: Hametner
authors: Johannes
authors: J
authors: Fröhlich
mesh_terms: D060326:Chemistry Techniques, Synthetic; D005965:Glucuronates / Q000138:chemical synthesis* / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry; D013997:Time Factors
chemical_list: D005965:Glucuronates; D012825:Silicon