Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments
(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.
(Less)
- 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
- 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}}, }