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- Nilsson, Ulf, et al.
(author)
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Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments
- 1994
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In: Carbohydrate Research. - : Elsevier BV. - 0008-6215. ; 252:C, s. 137-148
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Journal article (peer-reviewed)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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| 4. |
- Nilsson, Ulf, et al.
(author)
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Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments
- 1994
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In: Carbohydrate Research. - : Elsevier BV. - 0008-6215. ; 252:C, s. 117-136
-
Journal article (peer-reviewed)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 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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