Solid-Phase Synthesis of a Branched Hexasaccharide Using a Highly Efficient Synthetic Strategy

We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.

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Highly Efficient Peptide Synthesis: Automated Simultaneous Multiple Solid-Phase Synthesis and Peptide Library.

Journal of Synthetic Organic Chemistry Japan ◽

10.5059/yukigoseikyokaishi.52.347 ◽

1994 ◽

Vol 52 (5) ◽

pp. 347-358 ◽

Cited By ~ 1

Author(s):

Kiyoshi NOKIHARA

Keyword(s):

Peptide Synthesis ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Peptide Library ◽

Phase Synthesis ◽

Highly Efficient

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A Different Approach to the EGFR Inhibitor Gefitinib Involving Solid-Phase Synthesis

Synlett ◽

10.1055/s-0037-1610127 ◽

2018 ◽

Vol 29 (10) ◽

pp. 1346-1350 ◽

Cited By ~ 2

Author(s):

Luísa Carvalho ◽

André Sequeira ◽

Ana Lourenço ◽

Luísa Ferreira ◽

Paula Branco ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

Egfr Inhibitor ◽

Phase Synthesis ◽

Synthetic Strategy ◽

Colorimetric Assays ◽

First Time ◽

Synthesis Approach

An efficient solid-phase synthesis approach is here reported for the first time to prepare the EGFR inhibitor Gefitinib. The five-step synthetic strategy used FMP resin as the solid support, and FTIR and colorimetric assays were used to track the reaction’s progress. Gefitinib was obtained with an overall yield of 40%.

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Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives

Molecules ◽

10.3390/molecules24071406 ◽

2019 ◽

Vol 24 (7) ◽

pp. 1406 ◽

Cited By ~ 2

Author(s):

Eva Schütznerová ◽

Anna Krchňáková ◽

Viktor Krchňák

Keyword(s):

Natural Products ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Tetramic Acid ◽

Enol Ethers ◽

Phase Synthesis ◽

Wang Resin ◽

Synthetic Strategy ◽

Solid Phase Organic Synthesis ◽

Acid Labile

In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones.

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