Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, USA.
Org Biomol Chem. 2022 Sep 14;20(35):7006-7010. doi: 10.1039/d2ob01436j.
A mild and efficient cationic gold(I)-catalyzed -glycosylation methodology involving the use of bench-stable glycosyl -1,1-dimethylpropargyl carbamate donors has been developed. In the presence of 1-2 mol% [tris(2,4-di--butylphenyl)phosphite]gold(I) chloride and 5 mol% silver triflate, both "armed" and "disarmed" glycosyl -1,1-dimethylpropargyl carbamate donors react with various sugar acceptors at room temperature to afford the corresponding glycosides in good to excellent yields. These glycosyl -1,1-dimethylpropargyl carbamates are found to be orthogonal to regular phenyl thioglycoside donors. The utilization of this method has been demonstrated in the synthesis of a trisaccharide.
开发了一种温和高效的阳离子金（I）催化 -糖苷化方法，涉及使用稳定的糖基 -1,1-二甲基炔丙基氨基甲酸酯供体。在 1-2 mol% [三（2,4-二叔丁基苯基）膦]金（I）氯化物和 5 mol% 三氟甲磺酸银存在下，“武装”和“解除武装”的糖基 -1,1-二甲基炔丙基氨基甲酸酯供体在室温下与各种糖受体反应，以良好至优异的收率得到相应的糖苷。这些糖基 -1,1-二甲基炔丙基氨基甲酸酯与常规的苯基硫代糖苷供体正交。该方法已在三糖的合成中得到应用。
