Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration

Popis výsledku v původním jazyce

Nucleophilic displacement of the SN2-type has been one of the most favourite transformations in carbohydrate chemistry. In this respect, a hydroxyl group as a poor leaving one has to be activated prior to the attack of nucleophile. The Mitsunobu approachis based on the formation of a transient species (alkoxyphosphonium cation) employing triphenylphosphine (TPP)-dialkyl azodicarboxylate (DEAD) redox system. Although the mechanism of the Mitsunobu reaction has been extensively studied, there still exists considerable ambiguity as to factors influencing the outcome of the reaction.1,2-O-Isopropylidene-a-D-xylofuranose, 1,2-O-isopropylidene-a-D-ribofuranose and methyl 2,3-O-isopropylidene-b-D-ribofuranoside were subjected to the attack of miscellaneous nucleophiles , in the presence of DEAD and TPP. Furthermore, the stability of model compounds under the Mitsunobu conditions was investigated as well. The scope and limitation of the Mitsunobu methodology will be discussed with respect to:

Název v anglickém jazyce

Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration

Popis výsledku anglicky

Nucleophilic displacement of the SN2-type has been one of the most favourite transformations in carbohydrate chemistry. In this respect, a hydroxyl group as a poor leaving one has to be activated prior to the attack of nucleophile. The Mitsunobu approachis based on the formation of a transient species (alkoxyphosphonium cation) employing triphenylphosphine (TPP)-dialkyl azodicarboxylate (DEAD) redox system. Although the mechanism of the Mitsunobu reaction has been extensively studied, there still exists considerable ambiguity as to factors influencing the outcome of the reaction.1,2-O-Isopropylidene-a-D-xylofuranose, 1,2-O-isopropylidene-a-D-ribofuranose and methyl 2,3-O-isopropylidene-b-D-ribofuranoside were subjected to the attack of miscellaneous nucleophiles , in the presence of DEAD and TPP. Furthermore, the stability of model compounds under the Mitsunobu conditions was investigated as well. The scope and limitation of the Mitsunobu methodology will be discussed with respect to:

Druh

D - Stať ve sborníku

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2001

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název statě ve sborníku

3rd German-East-European Carbohydrate Workshop

ISBN

neuveden

ISSN

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e-ISSN

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Počet stran výsledku

1

Strana od-do

11-50

Název nakladatele

University Rostock

Místo vydání

Rostock

Místo konání akce

Guestrow

Datum konání akce

28. 2. 2001

Typ akce podle státní příslušnosti

EUR - Evropská akce

Kód UT WoS článku

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