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Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments

Nilsson, Ulf LU ; Ray, Asim K. and Magnusson, Göran LU (1994) In Carbohydrate Research 252(C). p.117-136
Abstract

The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of globotetraose [β-d-GalNAc-(1 → 3)-α-d-Gal-(1 → 4)-β-d-Gal-(1 → 4)-d-Glc] and the terminal trisaccharide, as well as the methyl α-glycoside 1 of the terminal disaccharide, were synthesised by silver trifluoromethanesulfonate-promoted β-glycosylation of suitably protected galactoside, galabioside, and globotrioside alcohols with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-galactopyranosyl chloride, followed by removal of protecting groups. Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3. The TMSEt glycoside of the terminal trisaccharide was... (More)

The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of globotetraose [β-d-GalNAc-(1 → 3)-α-d-Gal-(1 → 4)-β-d-Gal-(1 → 4)-d-Glc] and the terminal trisaccharide, as well as the methyl α-glycoside 1 of the terminal disaccharide, were synthesised by silver trifluoromethanesulfonate-promoted β-glycosylation of suitably protected galactoside, galabioside, and globotrioside alcohols with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-galactopyranosyl chloride, followed by removal of protecting groups. Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3. The TMSEt glycoside of the terminal trisaccharide was converted, via the 1-acetate, into the corresponding isobutyl (4) and 3-butylsulfonyl-2-[(butylsulfonyl)methyl]propy] (5) glycosides and into the TMSEt thioglycoside 6 via the glycosyl bromide.

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author
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publishing date
type
Contribution to journal
publication status
published
subject
in
Carbohydrate Research
volume
252
issue
C
pages
20 pages
publisher
Elsevier
external identifiers
  • scopus:0028039842
  • pmid:8137356
ISSN
0008-6215
DOI
10.1016/0008-6215(94)90010-8
language
English
LU publication?
yes
id
ab5e2855-f643-4e67-a4dd-d984045003ea
date added to LUP
2023-02-07 10:00:38
date last changed
2024-01-03 22:03:50
@article{ab5e2855-f643-4e67-a4dd-d984045003ea,
  abstract     = {{<p>The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of globotetraose [β-d-GalNAc-(1 → 3)-α-d-Gal-(1 → 4)-β-d-Gal-(1 → 4)-d-Glc] and the terminal trisaccharide, as well as the methyl α-glycoside 1 of the terminal disaccharide, were synthesised by silver trifluoromethanesulfonate-promoted β-glycosylation of suitably protected galactoside, galabioside, and globotrioside alcohols with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-galactopyranosyl chloride, followed by removal of protecting groups. Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3. The TMSEt glycoside of the terminal trisaccharide was converted, via the 1-acetate, into the corresponding isobutyl (4) and 3-butylsulfonyl-2-[(butylsulfonyl)methyl]propy] (5) glycosides and into the TMSEt thioglycoside 6 via the glycosyl bromide.</p>}},
  author       = {{Nilsson, Ulf and Ray, Asim K. and Magnusson, Göran}},
  issn         = {{0008-6215}},
  language     = {{eng}},
  month        = {{01}},
  number       = {{C}},
  pages        = {{117--136}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Research}},
  title        = {{Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments}},
  url          = {{http://dx.doi.org/10.1016/0008-6215(94)90010-8}},
  doi          = {{10.1016/0008-6215(94)90010-8}},
  volume       = {{252}},
  year         = {{1994}},
}