Interhalogens (ICI/IBr3) and AgOTf in thioglycoside activation; Synthesis of bislactam analogues of ganglioside GD3

Summary, in English

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.

• Författare: Andréas Meijer; Ulf Ellervik
• Avdelning/ar: Centrum för analys och syntes
• Publiceringsår: 2004
• Språk: Engelska
• Sidor: 6249-6256
• Publikation/Tidskrift/Serie: Journal of Organic Chemistry
• Volym: 69
• Issue: 19
• Länkar: http://dx.doi.org/10.1021/jo049184g
• Dokumenttyp: Artikel i tidskrift
• Förlag: The American Chemical Society (ACS)
• Ämne: Organic Chemistry
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 1520-6904