强心苷：2. 葡萄糖和半乳糖类似物的合成。

Cardiac glycosides: 2. Synthesis of glucose and galactose analogs.

作者信息

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

出版信息

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

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).

摘要

通过改良的柯尼希斯-克诺尔反应，将5种具有广泛不同C17β侧链基团的强心甾体苷元1a至5a转化为相应的β-D-葡萄糖苷1c至5c和β-D-半乳糖苷1e至5e。这些苷元包括洋地黄毒苷元（3β,14-二羟基-5β,14β-强心甾-20-(22)-烯内酯，1a）；(20R)-20,22-二氢洋地黄毒苷元（3β,14-二羟基-5β,14β,20R-强心甾醇，2a）；3β,14-二羟基-22-亚甲基-5β,14β,20S-强心甾醇（3a）；3β,14-二羟基-5β,14β-孕甾-20(E)-烯-21-羧酸甲酯（4a）；以及3β,14-二羟基-21-亚甲基-5β,14β-孕甾烷-21-羧酸甲酯（5a）。