Interhalogens (ICl/IBr) and AgOTf in Thioglycoside Activation; Synthesis of Bislactam Analogues of Ganglioside GD3
- 18 August 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (19) , 6249-6256
- https://doi.org/10.1021/jo049184g
Abstract
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.Keywords
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