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Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐ C ‐Glycoside Scaffolds
Recently, C ‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of C ‐glycosides, synthetic approaches en route to the C−C bond formation have gradually be...
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| Published in: | Advanced synthesis & catalysis 2024-04, Vol.366 (7), p.1484-1508 |
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| cites | cdi_FETCH-LOGICAL-c267t-f76a2a139be7d6e3e320540d373e28a1dafb214574fcc6b7588cdbde4fdcf30a3 |
| container_end_page | 1508 |
| container_issue | 7 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Sangwan, Rekha Azeem, Zanjila Kumar Mandal, Pintu |
| description | Recently,
C
‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of
C
‐glycosides, synthetic approaches en route to the C−C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches,
C
‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐
C
‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to
C
‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C−H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan
C
‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and
C
‐glycosylation sequence, c) metal‐catalyzed C−H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐
C
‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and
C
‐glycosylation sequence 2.3. Metal‐catalyzed C−H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook |
| doi_str_mv | 10.1002/adsc.202301490 |
| format | article |
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C
‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of
C
‐glycosides, synthetic approaches en route to the C−C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches,
C
‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐
C
‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to
C
‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C−H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan
C
‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and
C
‐glycosylation sequence, c) metal‐catalyzed C−H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐
C
‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and
C
‐glycosylation sequence 2.3. Metal‐catalyzed C−H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202301490</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Carbohydrates ; Cross coupling ; Glycosides ; Regioselectivity ; Stereoselectivity ; Synthesis ; Tryptophan</subject><ispartof>Advanced synthesis & catalysis, 2024-04, Vol.366 (7), p.1484-1508</ispartof><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c267t-f76a2a139be7d6e3e320540d373e28a1dafb214574fcc6b7588cdbde4fdcf30a3</citedby><cites>FETCH-LOGICAL-c267t-f76a2a139be7d6e3e320540d373e28a1dafb214574fcc6b7588cdbde4fdcf30a3</cites><orcidid>0000-0002-5813-9756</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Sangwan, Rekha</creatorcontrib><creatorcontrib>Azeem, Zanjila</creatorcontrib><creatorcontrib>Kumar Mandal, Pintu</creatorcontrib><title>Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐ C ‐Glycoside Scaffolds</title><title>Advanced synthesis & catalysis</title><description>Recently,
C
‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of
C
‐glycosides, synthetic approaches en route to the C−C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches,
C
‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐
C
‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to
C
‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C−H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan
C
‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and
C
‐glycosylation sequence, c) metal‐catalyzed C−H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐
C
‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and
C
‐glycosylation sequence 2.3. Metal‐catalyzed C−H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook</description><subject>Carbohydrates</subject><subject>Cross coupling</subject><subject>Glycosides</subject><subject>Regioselectivity</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><subject>Tryptophan</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNo9kN1KwzAYhoMoOKenHgc87vyStE17OIZug4Hg5nFI8-M6alOTTOmZl-A1eiV2Tnby_cDD-8KD0C2BCQGg91IHNaFAGZC0hDM0IjnJkpTk5fnpzuASXYWwAyC84HyE7LNRpo14qj9kq0zAstV4Hb2M5rUe3ug-pdcBr_s2bk2oA3YWL1vtmr75Yze-76LrtrL9-frGMzzMedMrF2pt8FpJa12jwzW6sLIJ5uZ_j9HL48NmtkhWT_PlbLpKFM15TCzPJZWElZXhOjfMMApZCppxZmghiZa2oiTNeGqVyiueFYXSlTap1coykGyM7o65nXfvexOi2Lm9b4dKwSAFxjJWlgM1OVLKuxC8saLz9Zv0vSAgDi7FwaU4uWS_pyFqvw</recordid><startdate>20240409</startdate><enddate>20240409</enddate><creator>Sangwan, Rekha</creator><creator>Azeem, Zanjila</creator><creator>Kumar Mandal, Pintu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-5813-9756</orcidid></search><sort><creationdate>20240409</creationdate><title>Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐ C ‐Glycoside Scaffolds</title><author>Sangwan, Rekha ; Azeem, Zanjila ; Kumar Mandal, Pintu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c267t-f76a2a139be7d6e3e320540d373e28a1dafb214574fcc6b7588cdbde4fdcf30a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Carbohydrates</topic><topic>Cross coupling</topic><topic>Glycosides</topic><topic>Regioselectivity</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><topic>Tryptophan</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sangwan, Rekha</creatorcontrib><creatorcontrib>Azeem, Zanjila</creatorcontrib><creatorcontrib>Kumar Mandal, Pintu</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sangwan, Rekha</au><au>Azeem, Zanjila</au><au>Kumar Mandal, Pintu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐ C ‐Glycoside Scaffolds</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2024-04-09</date><risdate>2024</risdate><volume>366</volume><issue>7</issue><spage>1484</spage><epage>1508</epage><pages>1484-1508</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Recently,
C
‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of
C
‐glycosides, synthetic approaches en route to the C−C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches,
C
‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐
C
‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to
C
‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C−H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan
C
‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and
C
‐glycosylation sequence, c) metal‐catalyzed C−H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐
C
‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and
C
‐glycosylation sequence 2.3. Metal‐catalyzed C−H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202301490</doi><tpages>25</tpages><orcidid>https://orcid.org/0000-0002-5813-9756</orcidid></addata></record> |
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| ispartof | Advanced synthesis & catalysis, 2024-04, Vol.366 (7), p.1484-1508 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_3040335399 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Carbohydrates Cross coupling Glycosides Regioselectivity Stereoselectivity Synthesis Tryptophan |
| title | Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐ C ‐Glycoside Scaffolds |
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