A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis.
Bibliographic Information
- Other Title
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- Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis
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Abstract
A "trimethyl lock" system has been known to facilitate lactonization reactions through what has been termed a stereopopulation contorl mechanism. We have found that a similar trimethyl lock system can also facilitate cyclic ether formation with the concomitant release of a carboxylic acid in the presence of anhydrous tetrabutylammonium fluoride. To study this base-mediated trimethyl lock-facilitated cyclic ether formation, we synthesized fifteen model compounds. All model compounds underwent base-mediated cyclic ether formation in high yields at 0°C to room temperature (r.t.) with the concomitant release of the attached carboxylate. Such a system potentially could be used for the development of a two-dimensional linker for solid phase peptide and organic synthesis.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 48 (2), 238-244, 2000
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679136610688
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- NII Article ID
- 110003635436
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 4978593
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- PubMed
- 10705512
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed