Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes

Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes

2,3,4-Tri-<i>O</i>-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cycl...

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Main Authors: Grzegorz Witkowski, Mykhaylo A. Potopnyk, Karolina Tiara, Anna Osuch-Kwiatkowska, Sławomir Jarosz
Format: Article
Language:English
Published: MDPI AG 2020-07-01
Series:Molecules
Subjects:
bicyclic sugar mimetics
stereoselective synthesis
Diels−Alder reaction
Wittig-type reaction
Online Access:https://www.mdpi.com/1420-3049/25/15/3357
id doaj-736f8d85d6bb48d29402ae4b0cbe8d72
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spelling doaj-736f8d85d6bb48d29402ae4b0cbe8d722020-11-25T03:25:50ZengMDPI AGMolecules1420-30492020-07-01253357335710.3390/molecules25153357Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived TrienesGrzegorz Witkowski0Mykhaylo A. Potopnyk1Karolina Tiara2Anna Osuch-Kwiatkowska3Sławomir Jarosz4Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland2,3,4-Tri-<i>O</i>-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.https://www.mdpi.com/1420-3049/25/15/3357bicyclic sugar mimeticsstereoselective synthesisDiels−Alder reactionWittig-type reaction
collection DOAJ
language English
format Article
sources DOAJ
author Grzegorz Witkowski
Mykhaylo A. Potopnyk
Karolina Tiara
Anna Osuch-Kwiatkowska
Sławomir Jarosz
spellingShingle Grzegorz Witkowski
Mykhaylo A. Potopnyk
Karolina Tiara
Anna Osuch-Kwiatkowska
Sławomir Jarosz
Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
Molecules
bicyclic sugar mimetics
stereoselective synthesis
Diels−Alder reaction
Wittig-type reaction
author_facet Grzegorz Witkowski
Mykhaylo A. Potopnyk
Karolina Tiara
Anna Osuch-Kwiatkowska
Sławomir Jarosz
author_sort Grzegorz Witkowski
title Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
title_short Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
title_full Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
title_fullStr Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
title_full_unstemmed Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> Derived Trienes
title_sort synthesis of highly oxygenated bicyclic carbasugars. remarkable difference in the reactivity of the d-<i>gluco</i> and d<i>-xylo-</i> derived trienes
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-07-01
description 2,3,4-Tri-<i>O</i>-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.
topic bicyclic sugar mimetics
stereoselective synthesis
Diels−Alder reaction
Wittig-type reaction
url https://www.mdpi.com/1420-3049/25/15/3357
work_keys_str_mv AT grzegorzwitkowski synthesisofhighlyoxygenatedbicycliccarbasugarsremarkabledifferenceinthereactivityofthediglucoianddixyloiderivedtrienes
AT mykhayloapotopnyk synthesisofhighlyoxygenatedbicycliccarbasugarsremarkabledifferenceinthereactivityofthediglucoianddixyloiderivedtrienes
AT karolinatiara synthesisofhighlyoxygenatedbicycliccarbasugarsremarkabledifferenceinthereactivityofthediglucoianddixyloiderivedtrienes
AT annaosuchkwiatkowska synthesisofhighlyoxygenatedbicycliccarbasugarsremarkabledifferenceinthereactivityofthediglucoianddixyloiderivedtrienes
AT sławomirjarosz synthesisofhighlyoxygenatedbicycliccarbasugarsremarkabledifferenceinthereactivityofthediglucoianddixyloiderivedtrienes
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