Non-acidic cleavage of Wang-derived ethers from solid support: Utilization of a mixed-bed scavenger for DDQ

Deegan, Tracy L.; Gooding, Owen W.; Baudart, Sylvie; Porco, John A.

doi:10.1016/s0040-4039(97)01078-2

Cited by 60 publications

(37 citation statements)

References 15 publications

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“…To avoid the use of acidic cleavage cocktails, we chose to explore two types of linkers, a silyloxy-based linker cleavable by tetra-n-butylammonium fluoride (TBAF) and an electronrich benzyl ether Wang-derived linker cleavable by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). 46,47 In the process of developing new linker technology, we also 50 which has been successfully used for the solid-phase syntheses of polyketides. 51 The diisopropylsilyl linker 50 facilitated incorporation of amino alcohols, practical building blocks for future combinatorial syntheses.…”

Section: Resultsmentioning

confidence: 99%

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Solid-Supported Nitroso Hetero Diels–Alder Reactions. 1. Acylnitroso Dienophiles: Scope and Limitations

Krchňák¹,

Moellmann²,

Dahse³

et al. 2008

J. Comb. Chem.

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Polymer-supported acylnitroso dienophiles were prepared and used in hetero Diels-Alder (HDA) reactions with a variety of dienes. The transient acylnitroso dienophiles were prepared in situ from immobilized hydroxamates, which were attached to solid supports via several linkers each cleavable by different cleavage reagents, and served for the synthesis of both N-unsubstituted and N-derivatized HDA adducts. Model compounds were used to (i) optimize reaction conditions for solid-supported HDA reactions, (ii) evaluate the outcome of the reactions with various dienes, (iii) compare relative reactivities of dienes, and (iv) assess the stability of HDA adducts toward cleavage conditions typically used in solid-phase syntheses. Cleaved products were submitted to biological assays, and the results are reported. The accompanying paper, focused on complementary arylnitroso HDA reactions, includes a comparison of both HDA reactions.

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Section: Resultsmentioning

confidence: 99%

“…The small amount of TFA ester that formed during cleavage 47 was hydrolyzed by addition of water. TFA-sensitive HDA adducts were cleanly cleaved in a high yield by DDQ.…”

Section: Resultsmentioning

confidence: 99%

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 1. Acylnitroso Dienophiles: Scope and Limitations

Krchňák¹,

Moellmann²,

Dahse³

et al. 2008

J. Comb. Chem.

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“…As DDQ is notoriously difficult to remove using column chromatography, a mixed resin-bed scavenging method was successfully applied to extract excess DDQ. 23 Polymer-supported ascorbate resin was used to reduce any excess DDQ to DDQH,…”

Section: Resultsmentioning

confidence: 99%

The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers

Lee

Ley

2003

Org. Biomol. Chem.

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A general asymmetric route to both enantiomers of polysphorin has been developed. The route utilizes polymer-supported reagents, catalysts and scavengers to minimise the need for aqueous work-up and chromatography. This includes application of a method to scavenge 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and a "catch-and-release" procedure to extract the resultant diol following Sharpless asymmetric dihydroxylation. A novel enzymatic selective protection and investigations of a new asymmetric dihydroxylation using microencapsulated osmium tetroxide were also investigated during the course of this study.

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“…Rink chloride 2.13 was converted to the Rink ether derivative 5.10 and cleaved to yield the required peptide-alcohol with 5% TFA/DCM. A potential 8.5 Immobilization via Amino Acid Side-Chain j303 byproduct from this route was the TFA ester [200,201]; however, the ester was readily hydrolyzed in aqueous sodium carbonate solution or simply by exposure to MeOH. Alternatively, 0.2 M HCl in DCM was used to cleave alcohols from the ether linker [82].…”

Section: Hydroxy Groupmentioning

confidence: 99%

Linkers for Solid‐Phase Peptide Synthesis

Soural

Hlaváč

Krchňák

2010

Amino Acids, Peptides and Proteins in Organic Chemistry

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Non-acidic cleavage of Wang-derived ethers from solid support: Utilization of a mixed-bed scavenger for DDQ

Cited by 60 publications

References 15 publications

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 1. Acylnitroso Dienophiles: Scope and Limitations

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 1. Acylnitroso Dienophiles: Scope and Limitations

The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers

Linkers for Solid‐Phase Peptide Synthesis

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