The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions

Linda Cronin; Manuela Tosin; Helge Müller-Bunz; Paul V. Murphy

doi:10.1016/j.carres.2006.10.023

The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions

Linda Cronin, Manuela Tosin, Helge Müller-Bunz, Paul V. Murphy

Centre for Synthesis and Chemical Biology

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

8 Citations (Scopus)

Abstract

The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.

Original language	English
Pages (from-to)	111-118
Number of pages	8
Journal	Carbohydrate Research
Volume	342
Issue number	1
DOIs	https://doi.org/10.1016/j.carres.2006.10.023
Publication status	Published - 15 Jan 2007
Externally published	Yes

Keywords

Amides
Anomerisation
Glucuronic acid
Glycosidation
Imidates
Lewis acid

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10.1016/j.carres.2006.10.023

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abstract = "The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.",

keywords = "Amides, Anomerisation, Glucuronic acid, Glycosidation, Imidates, Lewis acid",

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AU - Cronin, Linda

AU - Tosin, Manuela

AU - Müller-Bunz, Helge

AU - Murphy, Paul V.

PY - 2007/1/15

Y1 - 2007/1/15

N2 - The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.

AB - The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.

KW - Amides

KW - Anomerisation

KW - Glucuronic acid

KW - Glycosidation

KW - Imidates

KW - Lewis acid

UR - https://www.scopus.com/pages/publications/33845489262

U2 - 10.1016/j.carres.2006.10.023

DO - 10.1016/j.carres.2006.10.023

M3 - Article

SN - 0008-6215

VL - 342

SP - 111

EP - 118

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 1

ER -

The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions

Abstract

Keywords

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