Synthesis and absolute configuration assignment of 5-amino-1,3,5-triphenyl-pentane-1,3-diol stereoisomers
Starting from 2,4,6‐triphenylpyrylium perchlorate, 5‐amino‐1,3,5‐triphenyl‐pentane‐1,3‐diol stereoisomers 4 were obtained in a simple two‐step synthesis: reaction with hydroxylamine, and reduction with LAH of the resulting 2‐isoxazoline ketone derivative 2. The eight stereoisomers of 4 were separate...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2005, Vol.17 (1), p.63-72 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Uncuta, Cornelia Caraman, George B. Tanase, Catalin I. Bartha, Emeric Kravtsov, Victor CH Simonov, Yurii A. Lipkowski, Janus Vanthuyne, Nicolas Roussel, Christian |
| description | Starting from 2,4,6‐triphenylpyrylium perchlorate, 5‐amino‐1,3,5‐triphenyl‐pentane‐1,3‐diol stereoisomers 4 were obtained in a simple two‐step synthesis: reaction with hydroxylamine, and reduction with LAH of the resulting 2‐isoxazoline ketone derivative 2. The eight stereoisomers of 4 were separated in a single shot on a chiral stationary phase cellulose tris(3,5‐dimethylphenylcarbamate) (Chiralcel OD‐H). The absolute configuration of the title compounds, intermediate 2‐isoxazoline ketone 2 and isoxazoline alcohol derivative 3 were determined using a combination of diastereoselective synthesis, affiliation of the sign in chemical interconversion method, and X‐ray determination. 2‐Isoxazoline ketone 2 enantiomers and isoxazoline alcohol 3 enantiomers were obtained by chiral HPLC on Chiralpak AD column. 2‐Isoxazoline ketone 2 enantiomers can be racemized via a retro Michael addition. Chirality 17:63–72, 2005. © 2004 Wiley‐Liss, Inc. |
| doi_str_mv | 10.1002/chir.20098 |
| format | Article |
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The eight stereoisomers of 4 were separated in a single shot on a chiral stationary phase cellulose tris(3,5‐dimethylphenylcarbamate) (Chiralcel OD‐H). The absolute configuration of the title compounds, intermediate 2‐isoxazoline ketone 2 and isoxazoline alcohol derivative 3 were determined using a combination of diastereoselective synthesis, affiliation of the sign in chemical interconversion method, and X‐ray determination. 2‐Isoxazoline ketone 2 enantiomers and isoxazoline alcohol 3 enantiomers were obtained by chiral HPLC on Chiralpak AD column. 2‐Isoxazoline ketone 2 enantiomers can be racemized via a retro Michael addition. 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The eight stereoisomers of 4 were separated in a single shot on a chiral stationary phase cellulose tris(3,5‐dimethylphenylcarbamate) (Chiralcel OD‐H). The absolute configuration of the title compounds, intermediate 2‐isoxazoline ketone 2 and isoxazoline alcohol derivative 3 were determined using a combination of diastereoselective synthesis, affiliation of the sign in chemical interconversion method, and X‐ray determination. 2‐Isoxazoline ketone 2 enantiomers and isoxazoline alcohol 3 enantiomers were obtained by chiral HPLC on Chiralpak AD column. 2‐Isoxazoline ketone 2 enantiomers can be racemized via a retro Michael addition. Chirality 17:63–72, 2005. © 2004 Wiley‐Liss, Inc.</description><subject>absolute configuration determination</subject><subject>chemical correlation method</subject><subject>Chemical Sciences</subject><subject>chiral HPLC</subject><subject>Chromatography, High Pressure Liquid</subject><subject>configurational diversity</subject><subject>Crystallography, X-Ray</subject><subject>diastereoselective</subject><subject>Glycols - chemistry</subject><subject>isoxazoline reduction</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1vEzEQhi0Eomnhwg9Ae0Kiqos_195jFUFTKXy2qNwsZzNuDLt2sHeB_HscNpQbJ0vjZx6P50XoGSXnlBD2qt34dM4IafQDNKOSEVzz-stDNCO6aTAhgh2h45y_koLUXDxGR1RK0SjKZ8hf78KwgexzZcO6sqscu3GAqo3B-bsx2cHHUNmc_V3oIQxVdJXEtvchYnrGzyQekt9uIOw6vC33NsC-jtc-dlUeIEH0OfaQ8hP0yNkuw9PDeYI-v3l9M1_g5fvLq_nFErecCo1bB7xRREmqtKREKwWa1k6olZOMOkUYU0Cs5HrdKr5SVkgl61Y5LbQjoPkJejl5N7Yz2-R7m3YmWm8WF0uzrxEmqVAN_0EL-2Jityl-HyEPpve5ha4r34hjNrViQpYHC3g6gW2KOSdw92ZKzD4Esw_B_AmhwM8P1nHVw_ofeth6AegE_PQd7P6jMvPF1ae_Ujz1-LLVX_c9Nn0rU3Ilze27S_P29ubjh2tem5r_BmPxn6M</recordid><startdate>2005</startdate><enddate>2005</enddate><creator>Uncuta, Cornelia</creator><creator>Caraman, George B.</creator><creator>Tanase, Catalin I.</creator><creator>Bartha, Emeric</creator><creator>Kravtsov, Victor CH</creator><creator>Simonov, Yurii A.</creator><creator>Lipkowski, Janus</creator><creator>Vanthuyne, Nicolas</creator><creator>Roussel, Christian</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><general>Wiley</general><scope>BSCLL</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><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-1377-7081</orcidid><orcidid>https://orcid.org/0000-0003-2598-7940</orcidid></search><sort><creationdate>2005</creationdate><title>Synthesis and absolute configuration assignment of 5-amino-1,3,5-triphenyl-pentane-1,3-diol stereoisomers</title><author>Uncuta, Cornelia ; Caraman, George B. ; Tanase, Catalin I. ; Bartha, Emeric ; Kravtsov, Victor CH ; Simonov, Yurii A. ; Lipkowski, Janus ; Vanthuyne, Nicolas ; Roussel, Christian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3148-cfe397075178510877e816f47bf521f70227e0a538dc73b7a45756c7f848f0e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>absolute configuration determination</topic><topic>chemical correlation method</topic><topic>Chemical Sciences</topic><topic>chiral HPLC</topic><topic>Chromatography, High Pressure Liquid</topic><topic>configurational diversity</topic><topic>Crystallography, X-Ray</topic><topic>diastereoselective</topic><topic>Glycols - chemistry</topic><topic>isoxazoline reduction</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uncuta, Cornelia</creatorcontrib><creatorcontrib>Caraman, George B.</creatorcontrib><creatorcontrib>Tanase, Catalin I.</creatorcontrib><creatorcontrib>Bartha, Emeric</creatorcontrib><creatorcontrib>Kravtsov, Victor CH</creatorcontrib><creatorcontrib>Simonov, Yurii A.</creatorcontrib><creatorcontrib>Lipkowski, Janus</creatorcontrib><creatorcontrib>Vanthuyne, Nicolas</creatorcontrib><creatorcontrib>Roussel, Christian</creatorcontrib><collection>Istex</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uncuta, Cornelia</au><au>Caraman, George B.</au><au>Tanase, Catalin I.</au><au>Bartha, Emeric</au><au>Kravtsov, Victor CH</au><au>Simonov, Yurii A.</au><au>Lipkowski, Janus</au><au>Vanthuyne, Nicolas</au><au>Roussel, Christian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and absolute configuration assignment of 5-amino-1,3,5-triphenyl-pentane-1,3-diol stereoisomers</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2005</date><risdate>2005</risdate><volume>17</volume><issue>1</issue><spage>63</spage><epage>72</epage><pages>63-72</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>Starting from 2,4,6‐triphenylpyrylium perchlorate, 5‐amino‐1,3,5‐triphenyl‐pentane‐1,3‐diol stereoisomers 4 were obtained in a simple two‐step synthesis: reaction with hydroxylamine, and reduction with LAH of the resulting 2‐isoxazoline ketone derivative 2. The eight stereoisomers of 4 were separated in a single shot on a chiral stationary phase cellulose tris(3,5‐dimethylphenylcarbamate) (Chiralcel OD‐H). The absolute configuration of the title compounds, intermediate 2‐isoxazoline ketone 2 and isoxazoline alcohol derivative 3 were determined using a combination of diastereoselective synthesis, affiliation of the sign in chemical interconversion method, and X‐ray determination. 2‐Isoxazoline ketone 2 enantiomers and isoxazoline alcohol 3 enantiomers were obtained by chiral HPLC on Chiralpak AD column. 2‐Isoxazoline ketone 2 enantiomers can be racemized via a retro Michael addition. Chirality 17:63–72, 2005. © 2004 Wiley‐Liss, Inc.</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>15549713</pmid><doi>10.1002/chir.20098</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-1377-7081</orcidid><orcidid>https://orcid.org/0000-0003-2598-7940</orcidid></addata></record> |
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| subjects | absolute configuration determination chemical correlation method Chemical Sciences chiral HPLC Chromatography, High Pressure Liquid configurational diversity Crystallography, X-Ray diastereoselective Glycols - chemistry isoxazoline reduction Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Stereoisomerism |
| title | Synthesis and absolute configuration assignment of 5-amino-1,3,5-triphenyl-pentane-1,3-diol stereoisomers |
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