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

Meijer, Andréas LU and Ellervik, Ulf LU (2004) In Journal of Organic Chemistry 69(19). p.6249-6256
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.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
69
issue
19
pages
6249 - 6256
publisher
The American Chemical Society
external identifiers
  • wos:000223897700011
  • pmid:15357583
  • scopus:4644291544
ISSN
1520-6904
DOI
10.1021/jo049184g
language
English
LU publication?
yes
id
247479e0-0e68-4f4a-b390-42292f8e2a62 (old id 141175)
date added to LUP
2007-07-10 13:07:30
date last changed
2017-04-30 06:45:10
@article{247479e0-0e68-4f4a-b390-42292f8e2a62,
  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.},
  author       = {Meijer, Andréas and Ellervik, Ulf},
  issn         = {1520-6904},
  language     = {eng},
  number       = {19},
  pages        = {6249--6256},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Interhalogens (ICI/IBr3) and AgOTf in thioglycoside activation; Synthesis of bislactam analogues of ganglioside GD3},
  url          = {http://dx.doi.org/10.1021/jo049184g},
  volume       = {69},
  year         = {2004},
}