Aryl Sulfonates in Inversions at Secondary Carbohydrate Hydroxyl Groups: A New and Improved Route Toward 3-Azido-3-deoxy-beta-D-galactopyranosides

Summary, in English

A method of using benzenesulfonates and imidazylates as leaving groups at the secondary C3 galactopyranose carbon, instead of the commonly used less stable triflate leaving group, to facilitate scale-up and improve reproducibility is disclosed. The benzenesulfonates and imidazylates were proven to be significantly more stable than the corresponding triflates and the method was used to devise an improved route toward 3-azido-3-deoxy-beta-D-galactopyranosides.

• Author: Kristoffer Peterson; Alex Weymouth-Wilson; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2015
• Language: English
• Pages: 490-499
• Publication/Series: Journal of Carbohydrate Chemistry
• Volume: 34
• Issue: 8
• Full text: - 291 kB; Download statistics
• Links: http://dx.doi.org/10.1080/07328303.2015.1105248
• Document type: Journal article
• Publisher: Marcel Dekker
• Topic: Organic Chemistry
• Keywords: Benzenesulfonates; Imidazylates; Inversion; Galactose
• Status: Published
• ISBN/ISSN/Other: ISSN: 0732-8303