Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization
A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylide...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2018-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391800030S.pdf |
| _version_ | 1818759101677568000 |
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| author | Sahoo Laxminarayan Singhamahapatra Anadi Sahoo Satyanarayan |
| author_facet | Sahoo Laxminarayan Singhamahapatra Anadi Sahoo Satyanarayan |
| author_sort | Sahoo Laxminarayan |
| collection | DOAJ |
| description | A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions. |
| first_indexed | 2024-12-18T06:37:22Z |
| format | Article |
| id | doaj.art-0d94c899db144af499daaae43599f000 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-18T06:37:22Z |
| publishDate | 2018-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-0d94c899db144af499daaae43599f0002022-12-21T21:17:44ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212018-01-0183553954810.2298/JSC170905030S0352-51391800030SSynthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalizationSahoo Laxminarayan0Singhamahapatra Anadi1Sahoo Satyanarayan2District Forensic Science Laboratory, Puri, Odisha, IndiaSaraswati Degree Vidya Mandir, Neelakantha Nagar, Berhampur, Odisha, IndiaP.G. Department of Chemistry, Berhampur University, Berhampur, Odisha, IndiaA series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391800030S.pdfglycoconjugateregioselectivestereoselectivechemical synthesisclick reactionglycolipids |
| spellingShingle | Sahoo Laxminarayan Singhamahapatra Anadi Sahoo Satyanarayan Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization Journal of the Serbian Chemical Society glycoconjugate regioselective stereoselective chemical synthesis click reaction glycolipids |
| title | Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization |
| title_full | Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization |
| title_fullStr | Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization |
| title_full_unstemmed | Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization |
| title_short | Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization |
| title_sort | synthesis of 1 3 divalent glycoconjugates with diverse structures and their functionalization |
| topic | glycoconjugate regioselective stereoselective chemical synthesis click reaction glycolipids |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391800030S.pdf |
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