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

TETRAHEDRON LETTERS

卷:54

Article

Leidy, Michelle R.¹  Hoffman, J. Mason¹  Pongdee, Rongson¹ 

[1] Sewanee Univ South, Dept Chem, Sewanee, TN 37383 USA

关键词: Carbohydrates;    Deoxysugars;    Glycosides;    Natural products;    Suzuki-Miyaura;   

DOI  :  10.1016/j.tetlet.2013.10.031

来源: Elsevier

【 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.

【 授权许可】

Free