Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.

Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol or 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where the order to add NaH and a polyol si...

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Autores principales:	Takahiro Muraoka, Kota Adachi, Rainy Chowdhury, Kazushi Kinbara
Formato:	article
Lenguaje:	EN
Publicado:	Public Library of Science (PLoS) 2014
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/0e8a0dc39e3a43ac9a50ed9223269f8f
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spelling	oai:doaj.org-article:0e8a0dc39e3a43ac9a50ed9223269f8f2021-11-18T08:26:35ZTransetherification on polyols by intra- and intermolecular nucleophilic substitutions.1932-620310.1371/journal.pone.0091912https://doaj.org/article/0e8a0dc39e3a43ac9a50ed9223269f8f2014-01-01T00:00:00Zhttps://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24663293/?tool=EBIhttps://doaj.org/toc/1932-6203Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol or 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where the order to add NaH and a polyol significantly influences the yields of products. It was demonstrated that the protective group on the pentaerythritol skeleton is apparently transferred to the hydrophilic and hydrophobic chain molecules bearing a leaving group in one-step, and a protective group conversion from tosyl to benzyl was successful using a benzyl-appending triol to afford a desired product in 67% yield.Takahiro MuraokaKota AdachiRainy ChowdhuryKazushi KinbaraPublic Library of Science (PLoS)articleMedicineRScienceQENPLoS ONE, Vol 9, Iss 3, p e91912 (2014)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Takahiro Muraoka Kota Adachi Rainy Chowdhury Kazushi Kinbara Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
description	Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol or 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where the order to add NaH and a polyol significantly influences the yields of products. It was demonstrated that the protective group on the pentaerythritol skeleton is apparently transferred to the hydrophilic and hydrophobic chain molecules bearing a leaving group in one-step, and a protective group conversion from tosyl to benzyl was successful using a benzyl-appending triol to afford a desired product in 67% yield.
format	article
author	Takahiro Muraoka Kota Adachi Rainy Chowdhury Kazushi Kinbara
author_facet	Takahiro Muraoka Kota Adachi Rainy Chowdhury Kazushi Kinbara
author_sort	Takahiro Muraoka
title	Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
title_short	Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
title_full	Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
title_fullStr	Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
title_full_unstemmed	Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
title_sort	transetherification on polyols by intra- and intermolecular nucleophilic substitutions.
publisher	Public Library of Science (PLoS)
publishDate	2014
url	https://doaj.org/article/0e8a0dc39e3a43ac9a50ed9223269f8f
work_keys_str_mv	AT takahiromuraoka transetherificationonpolyolsbyintraandintermolecularnucleophilicsubstitutions AT kotaadachi transetherificationonpolyolsbyintraandintermolecularnucleophilicsubstitutions AT rainychowdhury transetherificationonpolyolsbyintraandintermolecularnucleophilicsubstitutions AT kazushikinbara transetherificationonpolyolsbyintraandintermolecularnucleophilicsubstitutions
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Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.

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