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1 article(s) from Furman, Bartłomiej

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

Michał M. Więcław and
Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

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Scheme 1: Our previous eﬀorts in the field of functionalization of sugar-derived lactams.

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Figure 1: Key concepts behind the goal of this work [34].

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Scheme 2: Preliminary experiment in search of a procedure for the synthesis of 2-(1H-tetrazol-5-yl)-iminosuga...

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Scheme 3: Synthesis of a new class of alkaloid scaﬀold using the presented methodology.

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Scheme 4: Synthesis of a new, chiral 2-(tetrazol-5-yl)-iminosugar based potential organocatalyst.

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Scheme 5: Principle behind Woerpel’s model for prediction of the direction of nucleophile addition to oxocarb...

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Scheme 6: Diﬀerence in conformational stability of glucose- and galactose-derived iminium cations and the maj...

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Figure 2: ORTEP structures of compounds 3a and 3e obtained by X-ray analysis. Hydrogen atoms and benzyl group...

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Figure 3: Proposed structures of compounds 5a and 2-epi-5a with ¹H-¹H couplings and NOE eﬀects shown.

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Scheme 7: Proposed reaction mechanism for the described Ugi–azide reaction variant.

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Scheme 8: Possible pathway for spontaneous imine formation. Values reported are in kcal·mol⁻¹.

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Scheme 9: A possible path for tetrazole formation in the described conditions. Values reported are in kcal·mol...

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Published 13 Jan 2021

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