New synthetic approaches to sugar ureas. Access to ureido-beta-cyclodextrins

作者：Lopez O; Maza S; Maya I; Fuentes J; Fernandez Bolanos JG^*

来源：Tetrahedron, 2005, 61(38): 9058-9069.

DOI：10.1016/j.tet.2005.07.041

• cyclodextrin
• triphosgene
• sugar isocyanates
• ureas
• mercury oxide
• two-phase system

An efficient method for the preparation of urea-bridged cyclodextrins using triphosgene in the isocyanation step in an aqueous two-phase system is reported. Per-O-acetylated glycopyranosylamines and 2-amino-2-deoxy-alpha and beta-D-glucose were also transformed into the corresponding isocyanates using either an aqueous two-phase or an anhydrous dichloromethane medium, and converted in situ into ureas. An alternative method for the preparation of sugar-derived ureas consisting of desulfurization of sugar thioureas with mercury oxide is also presented.

• 出版日期2005-9-19