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Comparative Study
. 1983 Jul;42(1):37-53.
doi: 10.1016/s0039-128x(83)90072-7.

Cardiac glycosides: 2. Synthesis of glucose and galactose analogs

M Kihara, K Yoshioka, E Kitatsuji, T Hashimoto, D S Fullerton, D C Rohrer
Comparative Study

Cardiac glycosides: 2. Synthesis of glucose and galactose analogs

M Kihara et al. Steroids. 1983 Jul.

Abstract

Five cardioactive steroid genins 1a to 5a of widely varying C17 beta-side groups were converted by modified Koenigs-Knorr reactions into the corresponding beta-D-glucosides 1c to 5c and beta-D-galactosides 1e to 5e. The genins included digitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta-card-20-(22)-enolide, 1a); (20R)-20, 22-dihydrodigitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta, 20R-cardanolde, 2a); 3 beta, 14-dihydroxy-22-methylene-5 beta, 14 beta, 20S-cardanolide (3a); methyl 3 beta, 14-dihydroxy-5 beta, 14 beta-pregn-20(E)-ene-21-carboxylate (4a); and methyl 3 beta, 14-dihydroxy-21-methylene-5 beta, 14 beta-pregnane-21-carboxylate (5a).

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