Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments
(1994) In Carbohydrate Research 252(C). p.137-148- Abstract
The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of the Forssman pentasaccharide [α-d-GalNAc-(1 → 3)-β-d-GalNAc-(1 → 3)-α-d-Gal-(1 → 4)-β-d-Gal-(1 → 4)-d-Glc] and the terminal tetrasaccharide, as well as the methyl glycosides 1 and 2 of the terminal di- and tri-saccharides, were synthesised by silver trifluoromethanesulfonate-promoted α-glycosylation of suitably protected mono-, di-, tri-, and tetrasaccharide alcohols with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranosyl bromide, followed by removal of protecting groups. The anomeric TMSEt group of the Forssman pentasaccharide and terminal tetrasaccharide was removed with trifluoroacetic acid-dichloromethane, to give the corresponding hemiacetal sugars 4 and 6.
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- author
- Nilsson, Ulf LU ; Ray, Asim K. and Magnusson, Göran LU
- organization
- publishing date
- 1994-01-15
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Carbohydrate Research
- volume
- 252
- issue
- C
- pages
- 12 pages
- publisher
- Elsevier
- external identifiers
-
- scopus:0028084562
- pmid:8137357
- ISSN
- 0008-6215
- DOI
- 10.1016/0008-6215(94)90011-6
- language
- English
- LU publication?
- yes
- id
- e64e8ad8-92de-4c4b-bc37-bd51c89e9413
- date added to LUP
- 2023-02-07 09:59:51
- date last changed
- 2024-01-03 22:03:50
@article{e64e8ad8-92de-4c4b-bc37-bd51c89e9413, abstract = {{<p>The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of the Forssman pentasaccharide [α-d-GalNAc-(1 → 3)-β-d-GalNAc-(1 → 3)-α-d-Gal-(1 → 4)-β-d-Gal-(1 → 4)-d-Glc] and the terminal tetrasaccharide, as well as the methyl glycosides 1 and 2 of the terminal di- and tri-saccharides, were synthesised by silver trifluoromethanesulfonate-promoted α-glycosylation of suitably protected mono-, di-, tri-, and tetrasaccharide alcohols with 3,4,6-tri-<i>O</i>-acetyl-2-azido-2-deoxy-α-d-galactopyranosyl bromide, followed by removal of protecting groups. The anomeric TMSEt group of the Forssman pentasaccharide and terminal tetrasaccharide was removed with trifluoroacetic acid-dichloromethane, to give the corresponding hemiacetal sugars 4 and 6.</p>}}, author = {{Nilsson, Ulf and Ray, Asim K. and Magnusson, Göran}}, issn = {{0008-6215}}, language = {{eng}}, month = {{01}}, number = {{C}}, pages = {{137--148}}, publisher = {{Elsevier}}, series = {{Carbohydrate Research}}, title = {{Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments}}, url = {{http://dx.doi.org/10.1016/0008-6215(94)90011-6}}, doi = {{10.1016/0008-6215(94)90011-6}}, volume = {{252}}, year = {{1994}}, }