Synthesis and development of novel silicon linkers for solid phase synthesis
Synthesis and development of novel silicon linkers for solid phase synthesis
A number of novel silicon linkers were synthesized starting from commercially available Merrifeid resin. After validation of the chemistry with a successful solution phase model, the optimized protocol was transferred to the solid phase, affording a range of silyloxy chloride in good and consistent values of loading. These linkers displayed excellent reactivity with primary, secondary and even tertiary alcohols and selective silylations of primary alcohols were also achieved. As part of the study a useful colorimetric test for the detection of polymer supported tertiary alcohols was developed and the utility of the linkers as supported protecting groups for alcohols was demonstrated under a range of experimental conditions, including strong bases, Grignard reagents, Suzuki, Heck, Sonogashira, RCM reactions and SPPS. The synthesis of the cyclopeptide Stylopeptide 1 was attempted employing the silyl linker as a supported side chain protecting group.
University of Southampton
Meloni, Marco Massimiliano
1080a758-3a47-4d50-8461-4754163f8a04
2004
Meloni, Marco Massimiliano
1080a758-3a47-4d50-8461-4754163f8a04
Meloni, Marco Massimiliano
(2004)
Synthesis and development of novel silicon linkers for solid phase synthesis.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A number of novel silicon linkers were synthesized starting from commercially available Merrifeid resin. After validation of the chemistry with a successful solution phase model, the optimized protocol was transferred to the solid phase, affording a range of silyloxy chloride in good and consistent values of loading. These linkers displayed excellent reactivity with primary, secondary and even tertiary alcohols and selective silylations of primary alcohols were also achieved. As part of the study a useful colorimetric test for the detection of polymer supported tertiary alcohols was developed and the utility of the linkers as supported protecting groups for alcohols was demonstrated under a range of experimental conditions, including strong bases, Grignard reagents, Suzuki, Heck, Sonogashira, RCM reactions and SPPS. The synthesis of the cyclopeptide Stylopeptide 1 was attempted employing the silyl linker as a supported side chain protecting group.
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Published date: 2004
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Local EPrints ID: 465353
URI: http://eprints.soton.ac.uk/id/eprint/465353
PURE UUID: e8e39cc4-cc51-4663-980a-f123217b446b
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Date deposited: 05 Jul 2022 00:39
Last modified: 16 Mar 2024 20:07
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Author:
Marco Massimiliano Meloni
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