Interhalogens (ICI/IBr3) and AgOTf in thioglycoside activation; Synthesis of bislactam analogues of ganglioside GD3
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/141175
- author
- Meijer, Andréas LU and Ellervik, Ulf LU
- organization
- publishing date
- 2004
- 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}}, }