Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks
4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, s...
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| Veröffentlicht in: | Journal of organic chemistry 2004-10, Vol.69 (21), p.7033-7037 |
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| container_end_page | 7037 |
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| container_issue | 21 |
| container_start_page | 7033 |
| container_title | Journal of organic chemistry |
| container_volume | 69 |
| creator | Caputo, Romualdo De Nisco, Mauro Festa, Pasquale Guaragna, Annalisa Palumbo, Giovanni Pedatella, Silvana |
| description | 4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers. |
| doi_str_mv | 10.1021/jo0493774 |
| format | Article |
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The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0493774</identifier><identifier>PMID: 15471449</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>4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Deoxy Sugars - chemical synthesis</subject><subject>Epoxy Compounds - chemistry</subject><subject>Exact sciences and technology</subject><subject>Hexoses - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1PHCEcBnBiaupqe_ALmLnY6IH652VgOda1tjbGNr6kvRFgwB2dHRRmkt1vX5rduJdy4cAvTx4ehA4JfCZAydlTBK6YlHwHTUhNAQsF_B2aAFCKGRVsD-3n_ATl1HX9Hu2RmkvCuZqg27tVP8x9bnMVQ8XxhY_LFe7wiembqsGnc7-M2ecqpLioZvM2ma66ib0zycb5qklm8NX52HZN2z9W5110z_kD2g2my_7j5j5AD5df72ff8fXPb1ezL9fYMKkG3EgPdjq1tAFVegXHDTAFhMpggwpMBAuSE0YkSGuNZV4G5WrqqeIMrGIH6NM69yXF19HnQS_a7HzXmd7HMWshlCg_pgWerqFLMefkg35J7cKklSag_w2o3wYs9mgTOtqFb7Zys1gBxxtgsjNdSKZ3bd46QQHYVBSH167Ng1--vZv0rIVkstb3v-40VT_I7z_qVl9uc43Lpc-Y-rLdfwr-BZ2wkSQ</recordid><startdate>20041015</startdate><enddate>20041015</enddate><creator>Caputo, Romualdo</creator><creator>De Nisco, Mauro</creator><creator>Festa, Pasquale</creator><creator>Guaragna, Annalisa</creator><creator>Palumbo, Giovanni</creator><creator>Pedatella, Silvana</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>20041015</creationdate><title>Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks</title><author>Caputo, Romualdo ; De Nisco, Mauro ; Festa, Pasquale ; Guaragna, Annalisa ; Palumbo, Giovanni ; Pedatella, Silvana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-d7e0b88b2d09005fc4a0390127fbf9f36fb074131707bbab3e7f9c52e29430b93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Deoxy Sugars - chemical synthesis</topic><topic>Epoxy Compounds - chemistry</topic><topic>Exact sciences and technology</topic><topic>Hexoses - chemical synthesis</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Caputo, Romualdo</creatorcontrib><creatorcontrib>De Nisco, Mauro</creatorcontrib><creatorcontrib>Festa, Pasquale</creatorcontrib><creatorcontrib>Guaragna, Annalisa</creatorcontrib><creatorcontrib>Palumbo, Giovanni</creatorcontrib><creatorcontrib>Pedatella, Silvana</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>Caputo, Romualdo</au><au>De Nisco, Mauro</au><au>Festa, Pasquale</au><au>Guaragna, Annalisa</au><au>Palumbo, Giovanni</au><au>Pedatella, Silvana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-10-15</date><risdate>2004</risdate><volume>69</volume><issue>21</issue><spage>7033</spage><epage>7037</epage><pages>7033-7037</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15471449</pmid><doi>10.1021/jo0493774</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Deoxy Sugars - chemical synthesis Epoxy Compounds - chemistry Exact sciences and technology Hexoses - chemical synthesis Organic chemistry Preparations and properties Stereoisomerism |
| title | Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks |
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