PARTIAL SYNTHESIS OF 25D-CHOLESTANOIC AND 25L-CHOLESTANOIC ACIDS FROM SOME COMMON BILE ACIDS
PARTIAL SYNTHESIS OF 25D-CHOLESTANOIC AND 25L-CHOLESTANOIC ACIDS FROM SOME COMMON BILE ACIDS
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DOI：
10.1021/jo00830a037
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发表时间：
1970-01-01
影响因子：
3.6
通讯作者：
BRIGGS, T
中科院分区：
文献类型：
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作者：
BRIGGS, T
讨论这里描述的合成不同于Bridgwater 4的方法，在电解过程中使用的不对称半酯。由于缺乏令人满意的制备光学纯的甲基琥珀酸半酯的方法，布里奇沃特使用d-或1-O-甲基谷氨酸的半酯。电解产生的高胆甾烷酸甲酯必须得到俄克拉荷马州大学医学院的一般研究资助（NIH）的部分支持。这项工作是在作者在康涅狄格州纽黑文市耶鲁大学医学院内科学系时开始的，在那里，它得到了USPHS赠款FR 00356-01和HE 03558-10的支持。出现了一个摘要：T。布里格斯，联邦检察官，26，3333（1967）中所述。(2)系统名称：胆酸，3 α，7 α，12 α-三羟基-5/3-胆烷酸;鹅脱氧胆酸，3 α，7 α-二羟基-5/3-胆烷酸;脱氧胆酸，3 α，12 α-二羟基-5/3-胆烷酸;石胆酸，3 α-羟基-5/3-胆烷酸。在胆甾烷酸的命名中，25 d对应于（25 R），25 l对应于（255）。(3)最近的评论：（a）比较生物化学与进化，G. A. D. Haslewood，J. Lipid Res.，（B）代谢，H. Danielsson和T. T. Tchen在“Metabolic Pathways”，第2卷，DM Greenberg编辑，学术出版社，纽约，NY，1968;（c）延长链胆汁酸和醇，T. Hoshita和T.和野，Advan。Lipid Res.，6，207（1968）。
DiscussionThe synthesis describedhere differs from the method of Bridgwater4 in the asymmetric half-ester used during electrolysis. Owing to the lack of a satisfactory method for preparing optically pure half-esters of methylsuccinic acid, Bridgwater used half-esters of d-or l-0-methylglutaric acid. Electrolysis produced methyl esters of homocholestanoic acids which had to be con-(1) Supportedin part by a general research support grant (NIH) from the University of Oklahoma School of Medicine. The work was begun while the author was in the Department of Internal Medicine, Yale University School of Medicine, New Haven, Conn., where it was supported by USPHS Grants FR 00356-01 and HE 03558-10. An abstract has appeared: T. Briggs, Federation Proc., 26, 3333 (1967).(2) Systematic names: cholic acid, 3a, 7a, 12a-trihydroxy-5/3-choIanoic acid; chenodeoxycholic acid, 3a, 7a-dihydroxy-5/3-cholanoic acid; deoxycholic acid, 3a, 12 «-dihydroxy-5/3-cholanoic acid; lithocholic acid, 3a-hydroxy-5/3-cholanoic acid. In the nomenclature of cholestanoic acids ac-cording to the sequence rule, 25d corresponds to (25R) and 25l to (255).(3) Recent reviews:(a) comparative biochemistry and evolution, G. A. D. Haslewood, J. Lipid Res., 8, 535 (1967);(b) metabolism, H. Danielsson and T. T. Tchen in “Metabolic Pathways,” Vol. 2, DM Greenberg, Ed., Academic Press Inc., New York, NY, 1968;(c) extended-chain bile acids and alcohols, T. Hoshita and T. Kazuno, Advan. Lipid Res., 6, 207 (1968).