A new photocleavable linker in solid-phase chemistry for ether cleavage

Citation
R. Glatthar et B. Giese, A new photocleavable linker in solid-phase chemistry for ether cleavage, ORG LETT, 2(15), 2000, pp. 2315-2317
Citations number
46
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2315 - 2317
Database
ISI
SICI code
1523-7060(20000727)2:15<2315:ANPLIS>2.0.ZU;2-1
Abstract
[GRAPHICS] We have designed a new linker (1) for the solid-phase synthesis that cleave s ether bonds photolytically. The linker was prepared in nine steps and anc hored to the support via an amide bond. Photocleavage is a two-step process in which the immobilized alcohols are released by photolytic generation of a radical that undergoes a spontaneous beta-bond scission. The pivaloyl li nker (1) was found to cleave off alcohols in high yields and purities. Only traces of acid (pH similar to 5.5) are necessary for an efficient cleavage .