Interhalogens (ICl/IBr) and AgOTf in thioglycoside activation; synthesis of bislactam analogues of ganglioside GD3
| Autor: | Andreas Meijer, Ulf Ellervik |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Reaction mechanism
Glycosylation Magnetic Resonance Spectroscopy Lactams Spectrophotometry Infrared Chemistry Stereochemistry Organic Chemistry Molecular Sequence Data General Medicine Chemical synthesis Mass Spectrometry chemistry.chemical_compound Halogens Carbohydrate Sequence Thioglycosides Yield (chemistry) Gangliosides Lactam Ganglioside GD3 Interhalogen |
| Zdroj: | The Journal of organic chemistry. 69(19) |
| ISSN: | 0022-3263 |
| Popis: | The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf. The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system. |
| Databáze: | OpenAIRE |
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