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dc.contributor.authorPati, Debasis
dc.contributor.authorFeng, Xiaoshuang
dc.contributor.authorHadjichristidis, Nikolaos
dc.contributor.authorGnanou, Yves
dc.date.accessioned2018-03-20T08:50:22Z
dc.date.available2018-03-20T08:50:22Z
dc.date.issued2018-03-15
dc.identifier.citationPati D, Feng X, Hadjichristidis N, Gnanou Y (2018) CO 2 as versatile carbonation agent of glycosides: Synthesis of 5- and 6-membered cyclic glycocarbonates and investigation of their ring-opening. Journal of CO2 Utilization 24: 564–571. Available: http://dx.doi.org/10.1016/j.jcou.2018.02.008.
dc.identifier.issn2212-9820
dc.identifier.doi10.1016/j.jcou.2018.02.008
dc.identifier.urihttp://hdl.handle.net/10754/627358
dc.description.abstractThis study demonstrates the successful use of CO as versatile carbonation agent for the synthesis of 5-membered and 6-membered bicyclic glycocarbonates from methyl α-d-mannopyranoside (MDM) and methyl α-d-galactopyranoside (MDG). On the one hand, these two sugars were cyclized into 5-membered glycocarbonates by mere reaction of CO with their hydroxyls either at cis-2,3 or cis-3,4 positions and without resorting to phosgene or its derivatives. The reactivity of the obtained 5-membered cyclic glycocarbonates were further tested with hexyl- and dodecyl amine. The self-assembling behavior of the formed alkyl glycosides in water was investigated and characterized by transmission electron microscope (TEM). On the other hand, secondary hydroxyls at 2- and 3- positions in MDM and MDG were first protected by a ketal group and by two ether, respectively before subjecting their respective 6-position hydroxyl to bromination. Their respective 6-bromo and 4-hydroxyl functions were subsequently reacted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and CO. The resulting 6-membered cyclic glycocarbonates were then polymerized using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) or DBU as organocatalyst. All the synthesized 5- and 6-membered cyclic glycocarbonates and polyglycocarbonates were thoroughly characterized by FT-IR, H, C NMR and MALDI-ToF and Gel Permeation Chromatography (GPC).
dc.description.sponsorshipThis research work is supported by KAUST under baseline funding (BAS/1/1374-01-01).
dc.publisherElsevier BV
dc.relation.urlhttps://www.sciencedirect.com/science/article/pii/S2212982017307047
dc.rightsNOTICE: this is the author’s version of a work that was accepted for publication in Journal of CO2 Utilization. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of CO2 Utilization, [24, , (2018-03-15)] DOI: 10.1016/j.jcou.2018.02.008 . © 2018. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectCarbon dioxide
dc.subjectCyclic carbonate
dc.subjectGlycoconjugates
dc.subjectGlycoside
dc.subjectPolyglycocarbonate
dc.titleCO 2 as versatile carbonation agent of glycosides: Synthesis of 5- and 6-membered cyclic glycocarbonates and investigation of their ring-opening
dc.typeArticle
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.identifier.journalJournal of CO2 Utilization
dc.eprint.versionPost-print
kaust.personPati, Debasis
kaust.personFeng, Xiaoshuang
kaust.personHadjichristidis, Nikolaos
kaust.personGnanou, Yves
kaust.grant.numberBAS/1/1374-01-01
dc.date.published-online2018-03-15
dc.date.published-print2018-03


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