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

ABSTRACT: The preparation of C-arylglycals has been accomplished 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.

SUBMITTER: Leidy MR

PROVIDER: S-EPMC4080724 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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

Leidy Michelle R MR Hoffman J Mason JM Pongdee Rongson R

Tetrahedron letters 20131201 50

The preparation of C-arylglycals has been accomplished 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 yi ...[more]

PMID: 24999287

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