Revision of the absolute configurations of bethosides B and C and their aglycone.

Revision of the absolute configurations of bethosides B and C and their aglycone.
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修改了 Bethoside B 和 C 及其苷元的绝对构型。

DOI:
10.1021/jo2012797
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发表时间:
2011
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
J. De Voss
J. De Voss
中科院分区:
--
文献类型:
--
作者:
Victoria L. Challinor;P. Hayes;P. Bernhardt;W. Kitching;R. Lehmann;J. De Voss

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根据采用 Horeau 方法的工作,甾体皂苷 B 和 C 的绝对立体化学先前被指定为 (22R,25R)。我们对 heloside A 和 B 的研究对最初的假设以及我们依赖它的结论产生了怀疑。在对其苷元进行 X 射线晶体学分析后,Bethoside B 和 C 的绝对构型被修改为 (22S,25R)。据报道,22R 和 22S 苷元的合成和全光谱表征有助于进一步确定该系列皂苷的立体化学归属。
The absolute stereochemistry of the steroidal saponins bethosides B and C was previously assigned as (22R,25R) on the basis of work that employed Horeau's method. Our studies of helosides A and B created doubt about both the original assignment and consequently our conclusion that relied upon it. The absolute configurations of bethosides B and C are revised to (22S,25R) following X-ray crystallographic analysis of their aglycone. Synthesis and full spectral characterization of both the 22R and 22S aglycones is reported to facilitate future stereochemical assignments in this series of saponins.