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一种从糖衍生的内酰胺合成 ADMDP 型氨基糖和奴吉利霉素衍生物的简便方法。

A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams.

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

Molecules. 2021 Sep 8;26(18):5459. doi: 10.3390/molecules26185459.

DOI:10.3390/molecules26185459
PMID:34576929
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8464940/
Abstract

An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel's or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives.

摘要

已经开发出一种高效合成诺吉利霉素和吡咯烷类亚氨基糖衍生物的方法。该策略基于Schwartz 试剂对糖衍生内酰胺的部分还原,以及氰化物或硅基烯醇醚的立体选择性亲核加成,这是由 Woerpel 或扩散控制模型决定的,得到氨基修饰的亚氨基糖,如 ADMDP 或更高的诺吉利霉素衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/fd1489764b96/molecules-26-05459-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/578f625db972/molecules-26-05459-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/bc92aa47a53c/molecules-26-05459-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/d986ee75be7f/molecules-26-05459-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/bdecaf0ff4af/molecules-26-05459-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/fd1489764b96/molecules-26-05459-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/578f625db972/molecules-26-05459-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/bc92aa47a53c/molecules-26-05459-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/d986ee75be7f/molecules-26-05459-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/bdecaf0ff4af/molecules-26-05459-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed58/8464940/fd1489764b96/molecules-26-05459-sch003.jpg

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本文引用的文献

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A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases.一种用于制备和发现新型亚氨基环醇作为糖苷酶抑制剂的通用合成策略。
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通过一锅法连续内酰胺还原/朱利耶-乌吉反应合成多羟基化哌啶和吡咯烷类肽模拟物。
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Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence.通过一锅法还原/曼尼希/迈克尔反应序列,由糖衍生的内酰胺合成多羟基喹嗪和中氮茚骨架。
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