A d-ribose-derived α-amino nitrile as a versatile intermediate for the collective synthesis of piperidine-type iminosugar C-glycosides

Xiang-Guo Hu; A. Daryl Ariawan; Luke Hunter

doi:10.1016/j.tetlet.2014.11.024

A d-ribose-derived α-amino nitrile as a versatile intermediate for the collective synthesis of piperidine-type iminosugar C-glycosides

Xiang-Guo Hu, A. Daryl Ariawan, Luke Hunter

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

13 Citations (Scopus)

Abstract

Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.

Original language	English
Pages (from-to)	7222-7225
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2014.11.024
Publication status	Published - 2014
Externally published	Yes

Keywords

Iminosugar
Iminocyclitol
Polyhydroxylated alkaloid
Iminium salt
Aminonitrile
Ring-closing metathesis

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10.1016/j.tetlet.2014.11.024

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abstract = "Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.",

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AU - Daryl Ariawan, A.

AU - Hunter, Luke

PY - 2014

Y1 - 2014

N2 - Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.

AB - Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.

KW - Iminosugar

KW - Iminocyclitol

KW - Polyhydroxylated alkaloid

KW - Iminium salt

KW - Aminonitrile

KW - Ring-closing metathesis

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DO - 10.1016/j.tetlet.2014.11.024

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

A d-ribose-derived α-amino nitrile as a versatile intermediate for the collective synthesis of piperidine-type iminosugar C-glycosides

Abstract

Keywords

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