Total synthesis of the Glc3Man N-glycan tetrasaccharide

S. C. Ennis, I. Cumpstey, A. J. Fairbanks, T. D. Butters, Muhammad Mukram Mohamed Mackeen, M. R. Wormald

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.

Original languageEnglish
Pages (from-to)9403-9411
Number of pages9
JournalTetrahedron
Volume58
Issue number46
DOIs
Publication statusPublished - 11 Nov 2002
Externally publishedYes

Fingerprint

Polysaccharides
Thioglycosides
Glycosylation
Stereoselectivity
Hydrogenation
Palladium
Acetic Acid
Hydroxyl Radical
Ether
Acetates
Ethanol
glucose tetrasaccharide

Keywords

  • Carbohydrates
  • Glycoproteins
  • Glycosidation
  • Thioglycosides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Ennis, S. C., Cumpstey, I., Fairbanks, A. J., Butters, T. D., Mohamed Mackeen, M. M., & Wormald, M. R. (2002). Total synthesis of the Glc3Man N-glycan tetrasaccharide. Tetrahedron, 58(46), 9403-9411. https://doi.org/10.1016/S0040-4020(02)01221-8

Total synthesis of the Glc3Man N-glycan tetrasaccharide. / Ennis, S. C.; Cumpstey, I.; Fairbanks, A. J.; Butters, T. D.; Mohamed Mackeen, Muhammad Mukram; Wormald, M. R.

In: Tetrahedron, Vol. 58, No. 46, 11.11.2002, p. 9403-9411.

Research output: Contribution to journalArticle

Ennis, SC, Cumpstey, I, Fairbanks, AJ, Butters, TD, Mohamed Mackeen, MM & Wormald, MR 2002, 'Total synthesis of the Glc3Man N-glycan tetrasaccharide', Tetrahedron, vol. 58, no. 46, pp. 9403-9411. https://doi.org/10.1016/S0040-4020(02)01221-8
Ennis SC, Cumpstey I, Fairbanks AJ, Butters TD, Mohamed Mackeen MM, Wormald MR. Total synthesis of the Glc3Man N-glycan tetrasaccharide. Tetrahedron. 2002 Nov 11;58(46):9403-9411. https://doi.org/10.1016/S0040-4020(02)01221-8
Ennis, S. C. ; Cumpstey, I. ; Fairbanks, A. J. ; Butters, T. D. ; Mohamed Mackeen, Muhammad Mukram ; Wormald, M. R. / Total synthesis of the Glc3Man N-glycan tetrasaccharide. In: Tetrahedron. 2002 ; Vol. 58, No. 46. pp. 9403-9411.
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