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

被引：17

作者：

Jin, J ^{[1
]}

Graybill, TL ^{[1
]}

Wang, MA ^{[1
]}

Davis, LD ^{[1
]}

Moore, ML ^{[1
]}

机构：

[1] SmithKline Beecham Pharmaceut, Dept Med Chem, King Of Prussia, PA 19406 USA

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2001年 / 3卷 / 01期

关键词：

D O I：

10.1021/cc000077j

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：97 / 101

页数：5

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