Synthesis and applications of fluorous silyl protecting groups with improved acid stability

Fluorous alkoxysilyl protecting groups have been developed and evaluated for their acid stability. tert-Butylphenyl-1 H,1 H,2 H,2 H-heptadecafluorodecyloxysilyl (BPFOS) ethers in particular were found to be surprisingly acid stable and allow simple protection-purification-deprotection schemes by liq...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 31; pp. 5667 - 5670
Main Authors Röver, Stephan, Wipf, Peter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.07.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BONDED PHASES
SEPARATION
LIQUID-CHROMATOGRAPHY
RETENTION
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ISSN0040-4039
1873-3581
DOI10.1016/S0040-4039(99)01106-5

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Summary:Fluorous alkoxysilyl protecting groups have been developed and evaluated for their acid stability. tert-Butylphenyl-1 H,1 H,2 H,2 H-heptadecafluorodecyloxysilyl (BPFOS) ethers in particular were found to be surprisingly acid stable and allow simple protection-purification-deprotection schemes by liquid-liquid extraction with FC-72/CH 3CN or by solid phase extraction with fluorous reverse phase silica gel. Fluorous alkoxysilyl protecting groups have been developed and evaluated for their acid stability. The tert-butyl-phenyl-1H,1H,2H,2H-heptadecafluorodecyloxysilyl (BPFOS) protecting group was found to be surprisingly acid stable.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01106-5