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Synthesis of the 2"-hydroxy, 4"-deoxy and 4"-epi analogues of β-D-GalNAc-(1→3)-α-D-Gal-(1→4)-β-D-Gal, the terminal trisaccharide of globotetraose

Nilsson, Ulf LU ; Wendler, Anikó LU and Magnusson, Göran LU (1994) In Acta chemica Scandinavica (Copenhagen, Denmark : 1989) 48(4). p.356-361
Abstract

Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-O-imidazol-1-yl-thiocarbonyloxy-2-phtha limido-beta-D - glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-bet a-D- galactopyranoside 10, followed by removal of protecting groups gave the 4"-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with... (More)

Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-O-imidazol-1-yl-thiocarbonyloxy-2-phtha limido-beta-D - glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-bet a-D- galactopyranoside 10, followed by removal of protecting groups gave the 4"-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2"-hydroxy and 4"-epi analogues 15 and 18, respectively.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Acta chemica Scandinavica (Copenhagen, Denmark : 1989)
volume
48
issue
4
pages
6 pages
publisher
Munksgaard Forlag
external identifiers
  • scopus:0028411871
  • pmid:8024905
ISSN
0904-213X
DOI
10.3891/acta.chem.scand.48-0356
language
English
LU publication?
yes
id
be08a779-b669-41d9-a49d-49c57ce0285b
date added to LUP
2023-02-07 09:48:57
date last changed
2024-01-03 22:02:28
@article{be08a779-b669-41d9-a49d-49c57ce0285b,
  abstract     = {{<p>Radical deoxygenation of methyl 3,6-di-<i>O</i>-benzoyl-2-deoxy-4-<i>O</i>-imidazol-1-yl-thiocarbonyloxy-2-phtha limido-beta-D - glucopyranoside 5 gave methyl 3,6-di-<i>O</i>-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-<i>O</i>-benzyl-4-<i>O</i>-(2,4,6-tri-<i>O</i>-benzyl-alpha-D-galactopyranosyl)-bet a-D- galactopyranoside 10, followed by removal of protecting groups gave the 4"-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-<i>O</i>-acetyl-2-deoxy-2- phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2,3,4,6-tetra-<i>O</i>-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2"-hydroxy and 4"-epi analogues 15 and 18, respectively.</p>}},
  author       = {{Nilsson, Ulf and Wendler, Anikó and Magnusson, Göran}},
  issn         = {{0904-213X}},
  language     = {{eng}},
  number       = {{4}},
  pages        = {{356--361}},
  publisher    = {{Munksgaard Forlag}},
  series       = {{Acta chemica Scandinavica (Copenhagen, Denmark : 1989)}},
  title        = {{Synthesis of the 2"-hydroxy, 4"-deoxy and 4"-epi analogues of β-D-GalNAc-(1→3)-α-D-Gal-(1→4)-β-D-Gal, the terminal trisaccharide of globotetraose}},
  url          = {{http://dx.doi.org/10.3891/acta.chem.scand.48-0356}},
  doi          = {{10.3891/acta.chem.scand.48-0356}},
  volume       = {{48}},
  year         = {{1994}},
}