Total synthesis of the Glc(3)Man N-glycan tetrasaccharide
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 glyco...
| Asıl Yazarlar: | , , , , , |
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| Materyal Türü: | Journal article |
| Dil: | English |
| Baskı/Yayın Bilgisi: |
2002
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| _version_ | 1826298488426594304 |
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| author | Ennis, S Cumpstey, I Fairbanks, A Butters, T Mackeen, M Wormald, M |
| author_facet | Ennis, S Cumpstey, I Fairbanks, A Butters, T Mackeen, M Wormald, M |
| author_sort | Ennis, S |
| collection | OXFORD |
| description | 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. © 2002 Published by Elsevier Science Ltd. |
| first_indexed | 2024-03-07T04:47:37Z |
| format | Journal article |
| id | oxford-uuid:d3dc11ab-61c4-4995-9a9e-a6241dbf529a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:47:37Z |
| publishDate | 2002 |
| record_format | dspace |
| spelling | oxford-uuid:d3dc11ab-61c4-4995-9a9e-a6241dbf529a2022-03-27T08:14:09ZTotal synthesis of the Glc(3)Man N-glycan tetrasaccharideJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d3dc11ab-61c4-4995-9a9e-a6241dbf529aEnglishSymplectic Elements at Oxford2002Ennis, SCumpstey, IFairbanks, AButters, TMackeen, MWormald, MThe 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. © 2002 Published by Elsevier Science Ltd. |
| spellingShingle | Ennis, S Cumpstey, I Fairbanks, A Butters, T Mackeen, M Wormald, M Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title | Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title_full | Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title_fullStr | Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title_full_unstemmed | Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title_short | Total synthesis of the Glc(3)Man N-glycan tetrasaccharide |
| title_sort | total synthesis of the glc 3 man n glycan tetrasaccharide |
| work_keys_str_mv | AT enniss totalsynthesisoftheglc3mannglycantetrasaccharide AT cumpsteyi totalsynthesisoftheglc3mannglycantetrasaccharide AT fairbanksa totalsynthesisoftheglc3mannglycantetrasaccharide AT butterst totalsynthesisoftheglc3mannglycantetrasaccharide AT mackeenm totalsynthesisoftheglc3mannglycantetrasaccharide AT wormaldm totalsynthesisoftheglc3mannglycantetrasaccharide |