γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

Y. Jagadeesh; A. T. Tran; B. Luo; N. Auberger; J. Désiré; S. Nakagawa; A. Kato; Y. Zhang; M. Sollogoub; Y. Blériot

doi:10.1039/c5ob00050e

γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

Y. Jagadeesh, A. T. Tran, B. Luo, N. Auberger, J. Désiré, S. Nakagawa, A. Kato, Y. Zhang, M. Sollogoub, Y. Blériot^*

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

Original language	English
Pages (from-to)	3446-3456
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	11
DOIs	https://doi.org/10.1039/c5ob00050e
State	Published - 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c5ob00050e

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title = "γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP",

abstract = "A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.",

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doi = "10.1039/c5ob00050e",

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T1 - γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

AU - Jagadeesh, Y.

AU - Tran, A. T.

AU - Luo, B.

AU - Auberger, N.

AU - Désiré, J.

AU - Nakagawa, S.

AU - Kato, A.

AU - Zhang, Y.

AU - Sollogoub, M.

AU - Blériot, Y.

PY - 2015

Y1 - 2015

N2 - A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

AB - A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

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U2 - 10.1039/c5ob00050e

DO - 10.1039/c5ob00050e

M3 - 学術論文

C2 - 25666467

AN - SCOPUS:84924301131

SN - 1477-0520

VL - 13

SP - 3446

EP - 3456

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

Abstract

ASJC Scopus subject areas

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