Novel silyl linkers for solid-phase synthesis
β Scribed by Marco M. Meloni; R.C.D. Brown; Peter D. White; Duncan Armour
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 161 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The syntheses of two silyl chloride resins, 2 and 10 are described starting from Merrifield resin, 3-methyl-1,3-butanediol and diphenyldichlorosilane or dimethyldichlorosilane, respectively. The silyl chloride resin 2 was used for the attachment of 1Β°a lcohols, 2Β°alcohols and phenols to the solid phase. A preliminary study of the stability of the diphenylsiloxane linker towards certain reaction conditions was also carried out. A more reactive silyl chloride resin 10 was found to be suitable for the attachment of 3Β°alcohols to the solid-phase.
π SIMILAR VOLUMES
Treatment of a free amino acid ester with CO 2 followed by exposure to a chlorosilane-containing polystyrene results in its attachment to the solid support. The newly formed silyl carbamate can be employed to build polypeptides at the carboxyl terminus. Cleavage of the (poly)peptide using aqueous HF
Commercially available (+)-ct-lipoic acid was employed as a novel, chemically robust linker for the immobilization of ketones. The utility of this thioacetal based linker in solid-phase synthesis was demonstrated by synthesizing several 4-acetylbiphenyls and 4-alkoxyacetophenones via Suzuki and Mits