ChemInform Abstract: Nucleosides. Part 55. Efficient Synthesis of Arabinoguanosine Building Blocks.

ChemInform ◽  
2010 ◽  
Vol 25 (27) ◽  
pp. no-no
Author(s):  
M. RESMINI ◽  
W. PFLEIDERER
Author(s):  
Dominka Fedorowicz ◽  
Sylwia Banach ◽  
Patrycja Koza ◽  
Rafał Frydrych ◽  
Katarzyna Ślepokura ◽  
...  

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...


2022 ◽  
Author(s):  
Zhi-Gang Yin ◽  
Xiong-Wei Liu ◽  
Hui-Juan Wang ◽  
Min Zhang ◽  
Xiong-Li Liu ◽  
...  

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.


Synlett ◽  
2021 ◽  
Author(s):  
Robin Van Den Hauwe ◽  
Mathias Elsocht ◽  
Charlie Hollanders ◽  
Steven Ballet

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.


Synlett ◽  
2019 ◽  
Vol 31 (05) ◽  
pp. 469-474 ◽  
Author(s):  
Fruzsina Demeter ◽  
Margaret Dah-Tsyr Chang ◽  
Yuan-Chuan Lee ◽  
Anikó Borbás ◽  
Mihály Herczeg

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.


2019 ◽  
Vol 15 ◽  
pp. 137-144 ◽  
Author(s):  
Teresa Mena-Barragán ◽  
José L de Paz ◽  
Pedro M Nieto

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.


Synthesis ◽  
2000 ◽  
Vol 2000 (11) ◽  
pp. 1579-1584 ◽  
Author(s):  
Arwin J. Brouwer ◽  
Menno C. F. Monnee ◽  
Rob M. J. Liskamp

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