Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration
Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a n...
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| Veröffentlicht in: | Journal of organic chemistry 2005-11, Vol.70 (24), p.9740-9754 |
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| container_end_page | 9754 |
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| container_issue | 24 |
| container_start_page | 9740 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Grayson, Elizabeth J Ward, Sarah J Hall, Alison L Rendle, Phillip M Gamblin, David P Batsanov, Andrei S Davis, Benjamin G |
| description | Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent−active reactivity tuning strategies. |
| doi_str_mv | 10.1021/jo051374j |
| format | Article |
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Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent−active reactivity tuning strategies.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051374j</identifier><identifier>PMID: 16292802</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. 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Org. Chem</addtitle><description>Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent−active reactivity tuning strategies.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Disulfides - chemical synthesis</subject><subject>Disulfides - chemistry</subject><subject>Doxorubicin - analogs & derivatives</subject><subject>Doxorubicin - chemical synthesis</subject><subject>Doxorubicin - chemistry</subject><subject>Exact sciences and technology</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>Glycosylation</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0Ltu1EAUBuARIiJLoOAFkBuQKBzm4rnRrQIJgXARSSS60fH4zOJl1g4zNmQ7Wl4zT4KjXbINpznF-fTr6CfkCaOHjHL2ctlTyYSulvfIjElOS2VpdZ_MKOW8FFyJffIw5yWdRkr5gOwzxS03lM_I5Ulc-z6vY_G6zWMMbYP51c3vP8XH_ifG4t8VhrZbFF8QFtgNufjVDt-K44jXbR2xmC9uVVfM44Bpkn33iOwFiBkfb_cBuTx-c3H0tjz7dHJ6ND8rQRg2lMHWggELitW-rrj1VhoAr9Eq4UMjLVJkRnuoKuAAAaGRzFjaMFZpbYM4IM83uVep_zFiHtyqzR5jhA77MTtlDDWU6gm-2ECf-pwTBneV2hWktWPU3Xbo7jqc7NNt6FivsNnJbWkTeLYFkD3EkKDzbd45LZiQSk6u3Lg2D3h9d4f03SkttHQXn89ddf7h_buvyjizywWfp3_G1E3d_efBv8XtlgQ</recordid><startdate>20051125</startdate><enddate>20051125</enddate><creator>Grayson, Elizabeth J</creator><creator>Ward, Sarah J</creator><creator>Hall, Alison L</creator><creator>Rendle, Phillip M</creator><creator>Gamblin, David P</creator><creator>Batsanov, Andrei S</creator><creator>Davis, Benjamin G</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051125</creationdate><title>Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration</title><author>Grayson, Elizabeth J ; Ward, Sarah J ; Hall, Alison L ; Rendle, Phillip M ; Gamblin, David P ; Batsanov, Andrei S ; Davis, Benjamin G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-f9b31a1f61bcb429c958aac7e963cfd59e0e187ca44a2aafead51890d114779f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Disulfides - chemical synthesis</topic><topic>Disulfides - chemistry</topic><topic>Doxorubicin - analogs & derivatives</topic><topic>Doxorubicin - chemical synthesis</topic><topic>Doxorubicin - chemistry</topic><topic>Exact sciences and technology</topic><topic>Glycosides - chemical synthesis</topic><topic>Glycosides - chemistry</topic><topic>Glycosylation</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Grayson, Elizabeth J</creatorcontrib><creatorcontrib>Ward, Sarah J</creatorcontrib><creatorcontrib>Hall, Alison L</creatorcontrib><creatorcontrib>Rendle, Phillip M</creatorcontrib><creatorcontrib>Gamblin, David P</creatorcontrib><creatorcontrib>Batsanov, Andrei S</creatorcontrib><creatorcontrib>Davis, Benjamin G</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Grayson, Elizabeth J</au><au>Ward, Sarah J</au><au>Hall, Alison L</au><au>Rendle, Phillip M</au><au>Gamblin, David P</au><au>Batsanov, Andrei S</au><au>Davis, Benjamin G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-11-25</date><risdate>2005</risdate><volume>70</volume><issue>24</issue><spage>9740</spage><epage>9754</epage><pages>9740-9754</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. 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| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2005-11, Vol.70 (24), p.9740-9754 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Disulfides - chemical synthesis Disulfides - chemistry Doxorubicin - analogs & derivatives Doxorubicin - chemical synthesis Doxorubicin - chemistry Exact sciences and technology Glycosides - chemical synthesis Glycosides - chemistry Glycosylation Molecular Conformation Organic chemistry Preparations and properties |
| title | Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration |
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