About: Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration

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Description	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 exist s 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: a) the order o 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 exist s 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: a) the order o (en)
Title	Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration (en)
skos:prefLabel	Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration (en)
skos:notation	RIV/60461373:22330/01:00004411!RIV/2004/MSM/223304/N
http://linked.open.../vavai/riv/strany	11:50
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM 223300006)
http://linked.open...vai/riv/dodaniDat	2004
http://linked.open...aciTvurceVysledku	Moravcová, Jitka
http://linked.open.../riv/druhVysledku	D - Článek ve sborníku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta potravinářské a biochemické technologie
http://linked.open...dnocenehoVysledku	687105
http://linked.open...ai/riv/idVysledku	RIV/60461373:22330/01:00004411
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Mitsunobu reaction;activation;hydroxy group (en)
http://linked.open.../riv/klicoveSlovo	activation Mitsunobu reaction hydroxy group
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http://linked.open...v/mistoKonaniAkce	Guestrow
http://linked.open...i/riv/mistoVydani	Neuveden
http://linked.open...i/riv/nazevZdroje	3rd German-East-European Carbohydrate Workshop
http://linked.open...in/vavai/riv/obor	CC
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http://linked.open...UplatneniVysledku	2001
http://linked.open...iv/tvurceVysledku	Moravcová, Jitka
http://linked.open...vavai/riv/typAkce	EUR - Evropská
http://linked.open.../riv/zahajeniAkce	2001-02-28 (xsd:date)
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number of pages	1 (xsd:int)
http://purl.org/ne...btex#hasPublisher	University Rostock
http://localhost/t...ganizacniJednotka	22330

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