Preparation of C-arylglycals via Suzuki-Miyaura cross-coupling of dihydropyranylphosphates

[摘要] The preparation of C-arylglycals has been accomplished by employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the corresponding C-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yield C-arylglycals in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

[发布日期] 2013-12-11

[关键词] Carbohydrates;Deoxysugars;Glycosides;Natural products;Suzuki-Miyaura