Stereoselective Synthesis of Nojirimycin α‑C‑Glycosides from a Bicyclic Acyliminium Intermediate: A Convenient Entry to N,C‑Biantennary Glycomimetics
A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type sp2-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp2-iminosugar O-glycosides or anomeric esters s...
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| Published in | ACS omega Vol. 7; no. 26; pp. 22394 - 22405 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
05.07.2022
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| Abstract | A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type sp2-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp2-iminosugar O-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including C-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of C-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-C-glycosides, which have been transformed into N,C-biantennary derivatives by reductive amination or thiourea-forming reactions. The thiourea adducts undergo intramolecular cyclization to bicyclic iminooxazolidine iminosugar α-C-glycosides upon acid treatment, broadening the opportunities for molecular diversity. A preliminary evaluation against a panel of commercial glycosidases validates the approach for finely tuning the inhibitory profile of glycomimetics. |
|---|---|
| AbstractList | A simple and efficient
method for the stereoselective synthesis
of nojirimycin α-
C
-glycoside derivatives has
been developed using a bicyclic carbamate-type sp
2
-iminosugar,
whose preparation on a gram scale has been optimized, as the starting
material. sp
2
-iminosugar
O
-glycosides
or anomeric esters serve as excellent precursors of acyliminium cations,
which can add nucleophiles, including
C
-nucleophiles.
The stereochemical outcome of the reaction is governed by stereoelectronic
effects, affording the target α-anomer with total stereoselectivity.
Thus, the judicious combination of
C
-allylation,
carbamate hydrolysis, cross-metathesis, and hydrogenation reactions
provides a very convenient entry to iminosugar α-
C
-glycosides, which have been transformed into
N
,
C
-biantennary derivatives by reductive amination or thiourea-forming
reactions. The thiourea adducts undergo intramolecular cyclization
to bicyclic iminooxazolidine iminosugar α-
C
-glycosides upon acid treatment, broadening the opportunities for
molecular diversity. A preliminary evaluation against a panel of commercial
glycosidases validates the approach for finely tuning the inhibitory
profile of glycomimetics. A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type sp2-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp2-iminosugar O-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including C-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of C-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-C-glycosides, which have been transformed into N,C-biantennary derivatives by reductive amination or thiourea-forming reactions. The thiourea adducts undergo intramolecular cyclization to bicyclic iminooxazolidine iminosugar α-C-glycosides upon acid treatment, broadening the opportunities for molecular diversity. A preliminary evaluation against a panel of commercial glycosidases validates the approach for finely tuning the inhibitory profile of glycomimetics. A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type sp2-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp2-iminosugar O-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including C-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of C-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-C-glycosides, which have been transformed into N,C-biantennary derivatives by reductive amination or thiourea-forming reactions. The thiourea adducts undergo intramolecular cyclization to bicyclic iminooxazolidine iminosugar α-C-glycosides upon acid treatment, broadening the opportunities for molecular diversity. A preliminary evaluation against a panel of commercial glycosidases validates the approach for finely tuning the inhibitory profile of glycomimetics.A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type sp2-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp2-iminosugar O-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including C-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of C-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-C-glycosides, which have been transformed into N,C-biantennary derivatives by reductive amination or thiourea-forming reactions. The thiourea adducts undergo intramolecular cyclization to bicyclic iminooxazolidine iminosugar α-C-glycosides upon acid treatment, broadening the opportunities for molecular diversity. A preliminary evaluation against a panel of commercial glycosidases validates the approach for finely tuning the inhibitory profile of glycomimetics. A simple and efficient method for the stereoselective synthesis of nojirimycin α- -glycoside derivatives has been developed using a bicyclic carbamate-type sp -iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp -iminosugar -glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including -nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of -allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α- -glycosides, which have been transformed into , -biantennary derivatives by reductive amination or thiourea-forming reactions. The thiourea adducts undergo intramolecular cyclization to bicyclic iminooxazolidine iminosugar α- -glycosides upon acid treatment, broadening the opportunities for molecular diversity. A preliminary evaluation against a panel of commercial glycosidases validates the approach for finely tuning the inhibitory profile of glycomimetics. |
| Author | González-Cuesta, Manuel García Fernández, José Manuel García-Moreno, M. Isabel Herrera-González, Irene Ortiz Mellet, Carmen |
| AuthorAffiliation | Instituto de Investigaciones Químicas (IIQ) Department of Organic Chemistry, Faculty of Chemistry |
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| Author_xml | – sequence: 1 givenname: Irene surname: Herrera-González fullname: Herrera-González, Irene organization: Department of Organic Chemistry, Faculty of Chemistry – sequence: 2 givenname: Manuel orcidid: 0000-0003-2778-9489 surname: González-Cuesta fullname: González-Cuesta, Manuel organization: Department of Organic Chemistry, Faculty of Chemistry – sequence: 3 givenname: M. Isabel surname: García-Moreno fullname: García-Moreno, M. Isabel organization: Department of Organic Chemistry, Faculty of Chemistry – sequence: 4 givenname: José Manuel orcidid: 0000-0002-6827-0387 surname: García Fernández fullname: García Fernández, José Manuel organization: Instituto de Investigaciones Químicas (IIQ) – sequence: 5 givenname: Carmen orcidid: 0000-0002-7676-7721 surname: Ortiz Mellet fullname: Ortiz Mellet, Carmen email: mellet@us.es organization: Department of Organic Chemistry, Faculty of Chemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35811898$$D View this record in MEDLINE/PubMed |
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| Snippet | A simple and efficient method for the stereoselective synthesis of nojirimycin α-C-glycoside derivatives has been developed using a bicyclic carbamate-type... A simple and efficient method for the stereoselective synthesis of nojirimycin α- -glycoside derivatives has been developed using a bicyclic carbamate-type sp... A simple and efficient method for the stereoselective synthesis of nojirimycin α- C -glycoside derivatives has been developed using a bicyclic carbamate-type... |
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| Title | Stereoselective Synthesis of Nojirimycin α‑C‑Glycosides from a Bicyclic Acyliminium Intermediate: A Convenient Entry to N,C‑Biantennary Glycomimetics |
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