Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol
Comprehensive Summary Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho‐nitro‐benzyl carbonate (oNBC) as a perma...
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| Veröffentlicht in: | Chinese journal of chemistry 2025-01, Vol.43 (2), p.169-174 |
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| container_end_page | 174 |
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| container_issue | 2 |
| container_start_page | 169 |
| container_title | Chinese journal of chemistry |
| container_volume | 43 |
| creator | Zheng, Jibin Chen, Hongyu Shang, Jintao Zhang, Lvfeng Liang, Youling Chang, Dongsheng Yang, You |
| description | Comprehensive Summary
Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho‐nitro‐benzyl carbonate (oNBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph3PO‐modulated glycosylation with strongly disarmed per‐O‐oNBC‐protected glycosyl ynenoates preferred to afford glycosides with excellent α‐selectivities via the β‐phosphonium transition state. Based on the oNBC‐mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.
The photolabile ortho‐nitro‐benzyl carbonate (oNBC) was utilized as a permanent hydroxyl protecting group for effective synthesis of digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters. |
| doi_str_mv | 10.1002/cjoc.202400866 |
| format | Article |
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Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho‐nitro‐benzyl carbonate (oNBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph3PO‐modulated glycosylation with strongly disarmed per‐O‐oNBC‐protected glycosyl ynenoates preferred to afford glycosides with excellent α‐selectivities via the β‐phosphonium transition state. Based on the oNBC‐mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.
The photolabile ortho‐nitro‐benzyl carbonate (oNBC) was utilized as a permanent hydroxyl protecting group for effective synthesis of digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202400866</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Carbohydrates ; Diglycerides ; Esters ; Glycolipids ; Glycosides ; Glycosylation ; Gold catalysis ; Oligosaccharides ; Photocatalysis ; Protecting groups ; Reagents ; Synthesis ; Synthetic methods</subject><ispartof>Chinese journal of chemistry, 2025-01, Vol.43 (2), p.169-174</ispartof><rights>2024 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH</rights><rights>2025 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2026-62dc0346959053b4cf70d3df6b10fee365d804fcd2239bdeb8eddefb38eba69c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcjoc.202400866$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.202400866$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zheng, Jibin</creatorcontrib><creatorcontrib>Chen, Hongyu</creatorcontrib><creatorcontrib>Shang, Jintao</creatorcontrib><creatorcontrib>Zhang, Lvfeng</creatorcontrib><creatorcontrib>Liang, Youling</creatorcontrib><creatorcontrib>Chang, Dongsheng</creatorcontrib><creatorcontrib>Yang, You</creatorcontrib><title>Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol</title><title>Chinese journal of chemistry</title><description>Comprehensive Summary
Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho‐nitro‐benzyl carbonate (oNBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph3PO‐modulated glycosylation with strongly disarmed per‐O‐oNBC‐protected glycosyl ynenoates preferred to afford glycosides with excellent α‐selectivities via the β‐phosphonium transition state. Based on the oNBC‐mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.
The photolabile ortho‐nitro‐benzyl carbonate (oNBC) was utilized as a permanent hydroxyl protecting group for effective synthesis of digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters.</description><subject>Carbohydrates</subject><subject>Diglycerides</subject><subject>Esters</subject><subject>Glycolipids</subject><subject>Glycosides</subject><subject>Glycosylation</subject><subject>Gold catalysis</subject><subject>Oligosaccharides</subject><subject>Photocatalysis</subject><subject>Protecting groups</subject><subject>Reagents</subject><subject>Synthesis</subject><subject>Synthetic methods</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQhiMEEqWwMltiTnFix0lGSKEFVbQSILFFjn1uU6VxsV1BmJiYeUaeBFdFMDL9N3zfne4PgtMIDyKM43Ox1GIQ45hinDG2F_QiFtEwxSzZ9zPGUcgwfToMjqxdej5NY9YLPmYL7XTDq7oBpI1b6K_3z7vamW1eQvvWNajgptItd4C4RRzNwKx4C61D404a_eqJmdEOhKvbORoZvVkjpQ1yC0D3XevD1hZphYb1nDdcOG29Mqy56Jp50wkwujkODhRvLJz8ZD94vL56KMbhZDq6KS4mofCPsZDFUmBCWZ7kOCEVFSrFkkjFqggrAMISmWGqhIxjklcSqgykBFWRDCrOckH6wdlu79ro5w1YVy71xrT-ZEkiSlOSMJp7arCjhNHWGlDl2tQrbroywuW263LbdfnbtRfynfDia-z-ocvidlr8ud-VVojY</recordid><startdate>20250115</startdate><enddate>20250115</enddate><creator>Zheng, Jibin</creator><creator>Chen, Hongyu</creator><creator>Shang, Jintao</creator><creator>Zhang, Lvfeng</creator><creator>Liang, Youling</creator><creator>Chang, Dongsheng</creator><creator>Yang, You</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20250115</creationdate><title>Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol</title><author>Zheng, Jibin ; Chen, Hongyu ; Shang, Jintao ; Zhang, Lvfeng ; Liang, Youling ; Chang, Dongsheng ; Yang, You</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2026-62dc0346959053b4cf70d3df6b10fee365d804fcd2239bdeb8eddefb38eba69c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><topic>Carbohydrates</topic><topic>Diglycerides</topic><topic>Esters</topic><topic>Glycolipids</topic><topic>Glycosides</topic><topic>Glycosylation</topic><topic>Gold catalysis</topic><topic>Oligosaccharides</topic><topic>Photocatalysis</topic><topic>Protecting groups</topic><topic>Reagents</topic><topic>Synthesis</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Jibin</creatorcontrib><creatorcontrib>Chen, Hongyu</creatorcontrib><creatorcontrib>Shang, Jintao</creatorcontrib><creatorcontrib>Zhang, Lvfeng</creatorcontrib><creatorcontrib>Liang, Youling</creatorcontrib><creatorcontrib>Chang, Dongsheng</creatorcontrib><creatorcontrib>Yang, You</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zheng, Jibin</au><au>Chen, Hongyu</au><au>Shang, Jintao</au><au>Zhang, Lvfeng</au><au>Liang, Youling</au><au>Chang, Dongsheng</au><au>Yang, You</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2025-01-15</date><risdate>2025</risdate><volume>43</volume><issue>2</issue><spage>169</spage><epage>174</epage><pages>169-174</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Comprehensive Summary
Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile ortho‐nitro‐benzyl carbonate (oNBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph3PO‐modulated glycosylation with strongly disarmed per‐O‐oNBC‐protected glycosyl ynenoates preferred to afford glycosides with excellent α‐selectivities via the β‐phosphonium transition state. Based on the oNBC‐mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.
The photolabile ortho‐nitro‐benzyl carbonate (oNBC) was utilized as a permanent hydroxyl protecting group for effective synthesis of digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202400866</doi><tpages>6</tpages></addata></record> |
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| ispartof | Chinese journal of chemistry, 2025-01, Vol.43 (2), p.169-174 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Carbohydrates Diglycerides Esters Glycolipids Glycosides Glycosylation Gold catalysis Oligosaccharides Photocatalysis Protecting groups Reagents Synthesis Synthetic methods |
| title | Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol |
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