Synthesis of β-D-Glucopyranosides of 12α-Epimers of 20S-Protopanaxadiol and Betulafolientriol

IF 0.8 4区化学 Q4 CHEMISTRY, MEDICINAL Chemistry of Natural Compounds Pub Date : 2024-09-19 DOI:10.1007/s10600-024-04464-7

L. N. Atopkina, A. I. Kalinovsky

{"title":"Synthesis of β-D-Glucopyranosides of 12α-Epimers of 20S-Protopanaxadiol and Betulafolientriol","authors":"L. N. Atopkina, A. I. Kalinovsky","doi":"10.1007/s10600-024-04464-7","DOIUrl":null,"url":null,"abstract":"β-D-Glucopyranosides of 3β, 12α,20S-trihydroxydammar-24-ene (1) and 3α,12α,20S-trihydroxydammar-24-ene (2), close structural analogs of ginsenoside-Rh2 and a metabolite of Panax ginseng glycosides (compound K), were synthesized. Glycosylation of 20S-hydroxydammar-24-ene-3,12-dione (5) and 3α-acetoxy-20S-hydroxydammar-24-en-12-one (6) by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (8) under classical Koenig-Knorr reaction conditions followed by deacetylation by NaOMe in MeOH gave free 20-O-β-D-glucopyranosides 10 and 13, treatment of which with NaBH4 in i-PrOH formed 20-O-β-D- glucopyranosides of the 12α-epimers of 20S-protopanaxadiol 11 and betulafolientriol 14. Condensation of 3β,12α,20S-trihydroxydammar-24-ene (1) and glycosyl donor 8 in the presence of Ag2O in CH2Cl2 followed by removal of the protecting groups gave 3-O-β-D-glucopyranoside 16; of 3α,12α,20S-trihydroxydammar-24-ene (2) under the same conditions, a mixture of 3- and 12-O-β-D-glucopyranosides 19 and 20.","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Natural Compounds","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10600-024-04464-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

Abstract

β-D-Glucopyranosides of 3β, 12α,20S-trihydroxydammar-24-ene (1) and 3α,12α,20S-trihydroxydammar-24-ene (2), close structural analogs of ginsenoside-Rh2 and a metabolite of Panax ginseng glycosides (compound K), were synthesized. Glycosylation of 20S-hydroxydammar-24-ene-3,12-dione (5) and 3α-acetoxy-20S-hydroxydammar-24-en-12-one (6) by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (8) under classical Koenig-Knorr reaction conditions followed by deacetylation by NaOMe in MeOH gave free 20-O-β-D-glucopyranosides 10 and 13, treatment of which with NaBH₄ in i-PrOH formed 20-O-β-D- glucopyranosides of the 12α-epimers of 20S-protopanaxadiol 11 and betulafolientriol 14. Condensation of 3β,12α,20S-trihydroxydammar-24-ene (1) and glycosyl donor 8 in the presence of Ag₂O in CH₂Cl₂ followed by removal of the protecting groups gave 3-O-β-D-glucopyranoside 16; of 3α,12α,20S-trihydroxydammar-24-ene (2) under the same conditions, a mixture of 3- and 12-O-β-D-glucopyranosides 19 and 20.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

20S-Protopanaxadiol 和 Betulafolientriol 的 12α-Epimers 的 β-D-Glucopyranosides 的合成

合成了 3β、12α、20S-三羟基达玛-24-烯 (1) 和 3α、12α、20S-三羟基达玛-24-烯 (2) 的 β-D-Glucopyranosides of 3β、12α、20S-三羟基达玛-24-烯 (1)，它们是人参皂甙-Rh2 的近似结构类似物，也是人参皂甙（化合物 K）的代谢物。20S-hydroxydammar-24-ene-3,12-dione (5) 和 3α-acetoxy-20S-hydroxydammar-24-en-12-one (6) 与 2,3,4,6-etra-O-acetyl-α-D-glucopyranosyl bromide (8) 在经典的 Koenig-Knorr 反应条件下进行糖基化，然后在 MeOH 中用 NaOMe 进行脱乙酰化，得到游离的 20-O-β-D-glucopyranosides 10 和 13、在 i-PrOH 中用 NaBH4 对其进行处理，可生成 20S-protopanaxadiol 11 和 betulafolientriol 14 的 12α-epimers 的 20-O-β-D- 吡喃葡萄糖苷。3β,12α,20S-三羟基达玛-24-烯（1）和糖基供体 8 在 Ag2O 存在下于 CH2Cl2 中缩合，然后去除保护基团，得到 3-O-β-D 吡喃葡萄糖苷 16；3α,12α,20S-三羟基达玛-24-烯（2）在相同条件下缩合，得到 3- 和 12-O-β-D 吡喃葡萄糖苷 19 和 20 的混合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Chemistry of Natural Compounds 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

265

审稿时长

7.8 months

期刊介绍： Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.