The 2-(triphenylsilyl)ethoxycarbonyl-("Tpseoc"-) group: a new silicon-based, fluoride cleavable oxycarbonyl protecting group highly orthogonal to the Boc-, Fmoc- and Cbz-groups
Golkowski, M; Ziegler, T
HERO ID
1070890
Reference Type
Journal Article
Year
2011
Language
English
PMID
| HERO ID | 1070890 |
|---|---|
| In Press | No |
| Year | 2011 |
| Title | The 2-(triphenylsilyl)ethoxycarbonyl-("Tpseoc"-) group: a new silicon-based, fluoride cleavable oxycarbonyl protecting group highly orthogonal to the Boc-, Fmoc- and Cbz-groups |
| Authors | Golkowski, M; Ziegler, T |
| Journal | Molecules |
| Volume | 16 |
| Issue | 6 |
| Page Numbers | 4695-4718 |
| Abstract | Starting from 2-(triphenylsilyl)ethanol a new oxycarbonyl protecting group cleavable by fluoride ion induced Peterson-elimination has been developed. Known 2-(triphenylsilyl)ethanol has been prepared from commercially available triphenylvinyl-silane by a hydroboration-oxidation sequence using the sterically hindered borane reagent 9-BBN. The silyl alcohol was subsequently transformed into its chloroformate, imidazolylcarboxylic acid ester and p-nitrophenyl carbonate and used in standard protocols for the formation of carbamates and carbonates. The Tpseoc group proved to be highly resistant against acidic conditions applied in removal of tert-butyl esters and the t-Boc-group. It also withstood catalytic hydrogenation, treatment with morpholine, methylhydrazine and Pd-reagents/allyl-scavanger combinations, conditions required to cleave Cbz-, Fmoc-, phthalimide- and Alloc-groups. The Tpseoc-group is cleaved upon treatment with TBAF/CsF at 0 °C or r.t. with cleavage times reaching from. |
| Doi | 10.3390/molecules16064695 |
| Pmid | 21654577 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Is Qa | No |