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

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Author

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.

Publishing year

2004

Language

English

Pages

6249-6256

Publication/Series

Journal of Organic Chemistry

Volume

69

Issue

19

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1520-6904