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Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments

Nilsson, Ulf LU ; Ray, Asim K. and Magnusson, Göran LU (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
; and
organization
publishing date
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}},
}