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

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.

SUBMITTER: Szczesniak P

PROVIDER: S-EPMC8464940 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Szcześniak Piotr P Grzeszczyk Barbara B Furman Bartłomiej B

Molecules (Basel, Switzerland) 20210908 18

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. ...[more]

PMID: 34576929

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