A. Umino, H. Hinou, H. Kuzuhara
Mar 1, 1998
Citations
0
Influential Citations
5
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
Abstract In the course of our studies on the synthesis of amphiphilic chitoheptaose derivatives carrying binary long hydrocarbon chains at the reducing sugar, tetradecyl 4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-2-tetradecanamido-β-D-glucopyranoside was prepared as a model. For general applicability, the 1,6-anhydro-2-deoxy-2-tetradecanamido-β-D-glucopyranosyl moiety was employed as a precursor of the reducing end. Acetolysis of the 1,6-anhydro ring using triethylsilyl triflate gave an oxazoline intermediate as a major product, accompanied by α-glycosyl acetate as a by-product. Immediate treatment of the mixture with 1-tetradecanol and protic acid followed by a separation work-up efficiently led to tetradecyl β-glycoside derivative.