L-Rhamnosylation: The Solvent is the Solution

Hidde Elferink; Christian Marcus Pedersen

doi:10.1002/ejoc.201601355

L-Rhamnosylation: The Solvent is the Solution

Hidde Elferink, Christian Marcus Pedersen

Kemisk Institut

12 Citationer (Scopus)

Abstract

Herein we present a systematic study of l-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the β selectivity, whereas nitrile solvents give almost exclusive α-selectively

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Udgave nummer	1
Sider (fra-til)	53-59
Antal sider	7
ISSN	1434-193X
DOI	https://doi.org/10.1002/ejoc.201601355
Status	Udgivet - 3 jan. 2017

Adgang til dokumentet

10.1002/ejoc.201601355

Citationsformater

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title = "L-Rhamnosylation: The Solvent is the Solution",

abstract = "Herein we present a systematic study of l-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the β selectivity, whereas nitrile solvents give almost exclusive α-selectively",

keywords = "Rhamnosylation, Glycosylation, Stereoselectivity, Reactivity, Solvent effects",

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AU - Pedersen, Christian Marcus

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N2 - Herein we present a systematic study of l-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the β selectivity, whereas nitrile solvents give almost exclusive α-selectively

AB - Herein we present a systematic study of l-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the β selectivity, whereas nitrile solvents give almost exclusive α-selectively

KW - Rhamnosylation

KW - Glycosylation

KW - Stereoselectivity

KW - Reactivity

KW - Solvent effects

U2 - 10.1002/ejoc.201601355

DO - 10.1002/ejoc.201601355

M3 - Journal article

SN - 1434-193X

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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