scholarly journals Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

2019 ◽  
Vol 15 ◽  
pp. 721-726 ◽  
Author(s):  
Clémence Moitessier ◽  
Ahmad Rifai ◽  
Pierre-Edouard Danjou ◽  
Isabelle Mallard ◽  
Francine Cazier-Dennin
Keyword(s):  
Building Blocks ◽  
Efficient Synthesis ◽  
Oxidation Step ◽  
Fluorimetric Analysis ◽  
Molecular Architectures

4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing to the addition of a protecting step of the unstable key intermediate 4,5-dihydroisobenzofuran-5-ol. Oxidation and deprotection steps were also studied in order to provide an effective availability of these two dialdehyde compounds that may increase their future applications.

Controlling chirality in the synthesis of 4 + 4 diastereomeric amine macrocycles derived from trans-1,2-diaminocyclopentane and 2,6-diformylpyridine.

2022 ◽  
Author(s):  
Dominka Fedorowicz ◽  
Sylwia Banach ◽  
Patrycja Koza ◽  
Rafał Frydrych ◽  
Katarzyna Ślepokura ◽  
...  
Keyword(s):  
Building Blocks ◽  
Efficient Synthesis

A few suitably long dialdehyde and primary diamine building blocks of a predetermined chirality have been designed and synthesized to enable controlled and efficient synthesis of all 6 possible diastereomers...

Design, synthesis and evaluation of structurally diverse ortho-acylphenol-diindolylmethane hybrids as anticancer agents

2022 ◽  
Author(s):  
Zhi-Gang Yin ◽  
Xiong-Wei Liu ◽  
Hui-Juan Wang ◽  
Min Zhang ◽  
Xiong-Li Liu ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Anticancer Agents ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Design Synthesis ◽  
Pyrone Ring ◽  
Ring Opening Reaction ◽  
First Time

A highly efficient synthesis of structurally diverse ortho-acylphenol–diindolylmethane hybrids 3 using carboxylic acid-activated chromones as versatile synthetic building blocks is reported here for the first time, through 1,4-nucleophilic addition and followed by a decarboxylation and pyrone ring opening reaction process.

Efficient synthesis of polysubstituted 1,5-benzodiazepinone dipeptide mimetics via an Ugi-4CR-Ullmann condensation sequence

Synlett ◽  
2021 ◽  
Author(s):  
Robin Van Den Hauwe ◽  
Mathias Elsocht ◽  
Charlie Hollanders ◽  
Steven Ballet
Keyword(s):  
Building Blocks ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Rapid Construction ◽  
Ligand Free

An efficient three step synthesis towards 3-amino-1,4-benzodiazepin-2-one derivatives is presented. The versatile Ugi-4-component reaction (Ugi-4CR) and Boc-deprotection is followed by a ligand-free Ullmann condensation. This protocol allows the rapid construction of a diverse array of substituted 1,5-benzodiazepinones. Since Ugi-based products are typically limited by their ‘inert’ C-terminal amides, the use of a convertible (‘cleavable’) isocyanide was envisaged and resulted in building blocks that can be made SPPS-compatible. To demonstrate the potential of this novel synthetic route, the design and preparation of novel phenylurea-1,5-bezondiazepin-4(5H)-one dipeptide mimetics with potential CCK2-antagonist properties is reported.

An Efficient Synthesis of the Pentasaccharide Repeating Unit of Pseudomonas aeruginosa Psl Exopolysaccharide

Synlett ◽  
2019 ◽  
Vol 31 (05) ◽  
pp. 469-474 ◽  
Author(s):  
Fruzsina Demeter ◽  
Margaret Dah-Tsyr Chang ◽  
Yuan-Chuan Lee ◽  
Anikó Borbás ◽  
Mihály Herczeg
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Coupling Reaction ◽  
Building Blocks ◽  
Bacterial Biofilm ◽  
Efficient Synthesis ◽  
Negative Bacterium ◽  
Resistant Species ◽  
Promising Therapeutic Target ◽  
Polysaccharide Synthesis ◽  
Life Threatening

Pseudomonas aeruginosa is a biofilm-forming Gram-negative bacterium and a leading cause of life-threatening nosocomial infections. The polysaccharide synthesis locus (Psl) exopolysaccharide of P. aeruginosa is a key constituent of the defending bacterial biofilm layer and is a promising therapeutic target for resistant species. The Psl exopolysaccharide is built up from repeating pentasaccharide units which contain one α- and two β-mannosidic linkages, and one l-rhamnose and one d-glucose moieties. The preparation of this pentasaccharide was first described by Boons et al. in a 34-step synthesis. Based on their work, we have developed a new and effective pathway for the synthesis of the repeating pentasaccharide unit of the Psl exopolysaccharide. We have succeeded in simplifying the synthesis of the l-rhamnose and the α-selective d-mannose building blocks. Furthermore, taking advantage of a chemoselective pre-activation-based β-mannosylation, we directly prepare a thioglycoside disaccharide donor and use it in the next coupling reaction without further transformation. The pentasaccharide, in the form of a p-methoxyphenyl glycoside, is prepared in 26 steps, which is suitable for biological testing.

scholarly journals Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

2019 ◽  
Vol 15 ◽  
pp. 137-144 ◽  
Author(s):  
Teresa Mena-Barragán ◽  
José L de Paz ◽  
Pedro M Nieto
Keyword(s):  
Chondroitin Sulfate ◽  
Exploratory Study ◽  
Glucuronic Acid ◽  
Building Blocks ◽  
Significant Loss ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
The Impact

Here, we present an exploratory study on the fluorous-assisted synthesis of chondroitin sulfate (CS) oligosaccharides. Following this approach, a CS tetrasaccharide was prepared. However, in contrast to our previous results, a significant loss of β-selectivity was observed in [2 + 2] glycosylations involving N-trifluoroacetyl-protected D-galactosamine donors and D-glucuronic acid (GlcA) acceptors. These results, together with those obtained from experiments employing model monosaccharide building blocks, highlight the impact of the glycosyl acceptor structure on the stereoselectivity of glycosylation reactions. Our study provides useful data about the substitution pattern of GlcA units for the efficient synthesis of CS oligomers.

Sign in / Sign up

Export Citation Format

Share Document