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
(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
- Nilsson, Ulf LU ; Wendler, Anikó LU and Magnusson, Göran LU
- organization
- publishing date
- 1994-04
- 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
-
- pmid:8024905
- scopus:0028411871
- 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}}, }