The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides

Mads Heuckendorff; Christian Marcus Pedersen; Mikael Bols

doi:10.1021/ol202308y

The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides

Mads Heuckendorff, Christian Marcus Pedersen, Mikael Bols

Kemisk Institut

22 Citationer (Scopus)

Abstract

Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	13
Udgave nummer	22
Sider (fra-til)	5956–5959
Antal sider	4
ISSN	1523-7060
DOI	https://doi.org/10.1021/ol202308y
Status	Udgivet - 18 nov. 2011

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10.1021/ol202308y

Citationsformater

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title = "The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides",

abstract = "Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.",

author = "Mads Heuckendorff and Pedersen, {Christian Marcus} and Mikael Bols",

year = "2011",

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doi = "10.1021/ol202308y",

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journal = "Organic Letters",

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T1 - The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides

AU - Heuckendorff, Mads

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2011/11/18

Y1 - 2011/11/18

N2 - Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.

AB - Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.

U2 - 10.1021/ol202308y

DO - 10.1021/ol202308y

M3 - Journal article

C2 - 22007683

SN - 1523-7060

VL - 13

SP - 5956

EP - 5959

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides

Abstract

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