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

Piotr Szcześniak,Bartłomiej Furman,Barbara Grzeszczyk

doi:10.3390/molecules26185459

Piotr Szcześniak, Bartłomiej Furman + Show 1 more

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https://doi.org/10.3390/molecules26185459

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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.

Highlights

[24].work, In ourwe previous work, we found that the furanosyl and pyranosyl imines can be obtained from sugar-dethat thewe furanosyl andthe pyranosyl imines can be obtained sugar-derived lactams via work, found that furanosyl and pyranosyl imines from can be obtained from sugar-delactams via a Schwartz’s-reagent-mediated partial reduction in [25]
[25,26,27], we report the flexible and robust access to amino-iminosugars, such we report the flexible and robust access to amino-iminosugars, such as and zation [25,26,27], we report the flexible and robust access to amino-iminosugars, such as and higher derivatives, via a glucoor arabino-lactam reduction/cyanide ion or higher derivatives, via aderivatives, gluco- or arabino-lactam ion or silyl enolion ether as ADMDP
Our synthesis synthesis of ofamino-modified amino-modifiediminosugars iminosugars started started with withthe thesynthesis synthesisof ofinitial initial

Summary

Introduction

Iminosugars are are aa large large group group of of carbohydrate carbohydrate analogues analogues that that have have received received aa lot lot of of Iminosugars attention due to their ability to inhibit enzymes responsible for the formation or cleavage attention due to their ability to inhibit enzymes responsible for the formation or cleavage of of glycosidic bonds [1,2,3,4,5]. Ramesh reported synthesisofvia deamination glycals [24].work, In ourwe previous work, we found that the furanosyl and pyranosyl imines can be obtained from sugar-dethat thewe furanosyl andthe pyranosyl imines can be obtained sugar-derived lactams via work, found that furanosyl and pyranosyl imines from can be obtained from sugar-delactams via a Schwartz’s-reagent-mediated partial reduction in [25]. [25,26,27], leading to, for example, highly functionalized pyrrolidine andiminosugars piperidine iminosugars viaone-pot a tandem one-pot reduction/Grignard reagent and piperidine via a tandem reduction/Grignard reagent allylpyrrolidine and piperidine iminosugars via a tandem one-pot reduction/Grignard or reagent or allyltributyltin addition sequence

2.Results

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