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- W2950544162 abstract "Two methods for stereoselective β-glycosylation of digitoxose were developed. The first achieved stereocontrol by a 1,3-participation of a N-methylurethane group under acid catalysis. The second utilized mercuric-ion catalyzed cleavage of thioglycosides and a 1,3-participation of a p-methoxybenzoyl group in a neutral medium. The first highly stereoselective and quite efficient synthesis of digitoxin (C7) was achieved by a combination of these methods. The furyl-substituted precursor IV of digitoxigenin (Scheme 1) was used as aglycone, and the furan group was converted to the unsaturated lactone of digitoxin by our known oxidation procedure (m-chloroperbenzoic acid/NaBH4) after the assembly of the carbohydrate portion of the molecule and its deblocking was completed." @default.
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- W2950544162 date "1985-07-02" @default.
- W2950544162 modified "2023-09-22" @default.
- W2950544162 title "ChemInform Abstract: ON CARDIOACTIVE STEROIDS. XVI. STEREOSELECTIVE β-GLYCOSYLATION OF DIGITOXOSE: THE SYNTHESIS OF DIGITOXIN" @default.
- W2950544162 cites W2139800396 @default.
- W2950544162 doi "https://doi.org/10.1002/chin.198526335" @default.
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