Convenient preparation of 4-formyl-3,5-dimethoxyphenol and its incorporation into linkers and resins for solid-phase synthesis

Jian Jin, Todd L. Graybill, Michelle A. Wang, Larry D. Davis, Michael L. Moore

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

4-Formyl-3,5-dimethoxyphenol (1) is a key synthetic intermediate used to prepare the BAL family (backbone amide linker) of acid-labile linkers and resins. The utility of these linkers and resins for solid-phase synthesis of both peptides and non-peptides has been amply demonstrated. In this article we report a simple and scalable procedure for preparation of isomerically pure 4-formyl-3,5-dimethoxyphenol (1) and its subsequent incorporation into a representative BAL linker and functionalized resin: 4-(4-formyl-3,5-dimethoxyphenoxy)-butanoic acid and 4-formyl-3,5-dimethoxyphenoxy-polystyrene, respectively. The procedures are reproducible, are readily scalable, and require no chromatography.

Original languageEnglish
Pages (from-to)97-101
Number of pages5
JournalJournal of Combinatorial Chemistry
Volume3
Issue number1
DOIs
StatePublished - Jan 2001
Externally publishedYes

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