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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthesis of Diverse C2-Glyco-Acyl Azides and -Ureas by Palladium-Catalyzed Carbonylation Coupling of 2-Iodoglycals

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Author(s):
Soares-Paulino, Antonio Augusto [1] ; Stefani, Helio A. [2]
Total Authors: 2
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Ave Prof Lineu Prestes 580, BR-05508000 Sao Paulo - Brazil
[2] Stefani, Helio A., Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Ave Prof Lineu Prestes 580, BR-05508000 Sao Paulo, Brazil.Soares-Paulino, Antonio Augusto, Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Ave Prof Lineu Prestes 580, BR-05508000 Sao Paulo - Brazil
Total Affiliations: 2
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2020, n. 25 JUN 2020.
Web of Science Citations: 0
Abstract

Herein, we describe the synthesis of acyl azides and acyl urea glycals, a new class of C-2 branched glycoconjugates, employing Pd-catalyzed carbonylative coupling. A new strategy was developed to obtain acyl azides by carbonylative coupling between 2-iodo-glycals and NaN(3)catalyzed by Pd(dba)(2)/Xantphos and carbon monoxide as a carbonyl source. Acyl azide glycals were used as synthetic intermediates in obtaining new acyl urea glycals via carbonylative coupling catalyzed by Pd(OAc)(2)and 1,10-Phen. Different glycal substrates, including disaccharide-type, were studied, and various acyl azides and acyl ureas were prepared. Reaction yields were moderate to high (31-99 %) and reaction time varying from short to long (0.5-20 h). (AU)

FAPESP's process: 14/50316-7 - Dimensions US-Biota São Paulo: Chemically mediated multi-trophic interaction diversity across tropical gradients
Grantee:Massuo Jorge Kato
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 18/10108-7 - Itramolecular Cycloaddition [2+2] Reactions Employing D-Glucal
Grantee:Antonio Augusto Soares Paulino
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 17/24821-4 - Carbonylative Coupling and Intramolecular Cycloaddition [2 + 2] Reactions Employing D-Glucal
Grantee:Helio Alexandre Stefani
Support Opportunities: Regular Research Grants