Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F01%3A00004411" target="_blank" >RIV/60461373:22330/01:00004411 - isvavai.cz</a>
Result on the web
—
DOI - Digital Object Identifier
—

Result language
angličtina
Original language name
Mitsunobu Activation of Pentose Hydroxyl Groups: a Synthetic Consideration
Original language 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 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:
Czech name
—
Czech description
—

Publication year
2001
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)