Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor

Alfred Hassner; Eliezer Falb; Abraham Nudelman; Amnon Albeck; Hugo E. Gottlieb

doi:10.1016/0040-4039(94)85229-4

Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor

Alfred Hassner
, Eliezer Falb
, Abraham Nudelman
, Amnon Albeck
, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

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

39 Scopus citations

Abstract

A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.

Original language	English
Pages (from-to)	2397-2400
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	15
DOIs	https://doi.org/10.1016/0040-4039(94)85229-4
State	Published - 11 Apr 1994

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10.1016/0040-4039(94)85229-4

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abstract = "A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.",

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T1 - Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor

AU - Hassner, Alfred

AU - Falb, Eliezer

AU - Nudelman, Abraham

AU - Albeck, Amnon

AU - E. Gottlieb, Hugo

PY - 1994/4/11

Y1 - 1994/4/11

N2 - A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.

AB - A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.

UR - https://www.scopus.com/pages/publications/0028231393

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SN - 0040-4039

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Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor

Abstract

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