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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 orcid (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
and
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 (ACS)
external identifiers
  • wos:000223897700011
  • pmid:15357583
  • scopus:4644291544
  • pmid:15357583
ISSN
1520-6904
DOI
10.1021/jo049184g
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
247479e0-0e68-4f4a-b390-42292f8e2a62 (old id 141175)
date added to LUP
2016-04-01 11:39:22
date last changed
2024-01-07 15:30:14
@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 (ACS)}},
  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}},
  doi          = {{10.1021/jo049184g}},
  volume       = {{69}},
  year         = {{2004}},
}