Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study

Shuai Wang; Dominique Lafont; Jani Rahkila; Benjamin Picod; Reko Leino; Sébastian Vidal

doi:10.1016/j.carres.2013.02.009

Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study

Shuai Wang, Dominique Lafont, Jani Rahkila, Benjamin Picod, Reko Leino, Sébastian Vidal

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

7 Citations (Scopus)

Abstract

Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.

Original language	Undefined/Unknown
Pages (from-to)	35–46
Number of pages	12
Journal	Carbohydrate Research
Volume	372
DOIs	https://doi.org/10.1016/j.carres.2013.02.009
Publication status	Published - 2013
MoE publication type	A1 Journal article-refereed

Keywords

Carbohydrate
Glycoside
Glycosylation
Pyridine acceptor
Trichloroacetimidate

Access to Document

10.1016/j.carres.2013.02.009

Cite this

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title = "Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study",

abstract = "Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.",

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author = "Shuai Wang and Dominique Lafont and Jani Rahkila and Benjamin Picod and Reko Leino and S{\'e}bastian Vidal",

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journal = "Carbohydrate Research",

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TY - JOUR

T1 - Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study

AU - Wang, Shuai

AU - Lafont, Dominique

AU - Rahkila, Jani

AU - Picod, Benjamin

AU - Leino, Reko

AU - Vidal, Sébastian

PY - 2013

Y1 - 2013

N2 - Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.

AB - Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.

KW - Carbohydrate

KW - Glycoside

KW - Glycosylation

KW - Pyridine acceptor

KW - Trichloroacetimidate

KW - Carbohydrate

KW - Glycoside

KW - Glycosylation

KW - Pyridine acceptor

KW - Trichloroacetimidate

KW - Carbohydrate

KW - Glycoside

KW - Glycosylation

KW - Pyridine acceptor

KW - Trichloroacetimidate

U2 - 10.1016/j.carres.2013.02.009

DO - 10.1016/j.carres.2013.02.009

M3 - Artikel

SN - 0008-6215

VL - 372

SP - 35

EP - 46

JO - Carbohydrate Research

JF - Carbohydrate Research

ER -