alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine
Efficient syntheses of methyl L-sibirosaminide and its C-3 epimer are described using L-allothreonine as the chiral educt. Amino acylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-allothreonine constitute the key carbon-carbon bond-forming steps. The resulting methyl and vin...
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| Veröffentlicht in: | Journal of organic chemistry 1985-02, Vol.50 (3), p.325-332 |
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| container_title | Journal of organic chemistry |
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| creator | Maurer, Peter J Knudsen, Christopher G Palkowitz, Alan D Rapoport, Henry |
| description | Efficient syntheses of methyl L-sibirosaminide and its C-3 epimer are described using L-allothreonine as the chiral educt. Amino acylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-allothreonine constitute the key carbon-carbon bond-forming steps. The resulting methyl and vinyl ketones are then converted to tertiary alcohols by a second organometallic addition, and the order of addition controls the stereochemistry at the new chiral center. Stereocontrolled functionalization of the vinyl group then leads to the amino sugars. Elaboration to the C-3 epimer of sibirosamine was achieved via a Pummerer oxidation route, while in the preparation of sibirosamine itself a selective tetraol oxidation route was used. |
| doi_str_mv | 10.1021/jo00203a008 |
| format | Article |
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Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine</title><source>ACS Publications</source><creator>Maurer, Peter J ; Knudsen, Christopher G ; Palkowitz, Alan D ; Rapoport, Henry</creator><creatorcontrib>Maurer, Peter J ; Knudsen, Christopher G ; Palkowitz, Alan D ; Rapoport, Henry</creatorcontrib><description>Efficient syntheses of methyl L-sibirosaminide and its C-3 epimer are described using L-allothreonine as the chiral educt. Amino acylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-allothreonine constitute the key carbon-carbon bond-forming steps. The resulting methyl and vinyl ketones are then converted to tertiary alcohols by a second organometallic addition, and the order of addition controls the stereochemistry at the new chiral center. Stereocontrolled functionalization of the vinyl group then leads to the amino sugars. Elaboration to the C-3 epimer of sibirosamine was achieved via a Pummerer oxidation route, while in the preparation of sibirosamine itself a selective tetraol oxidation route was used.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00203a008</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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Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Efficient syntheses of methyl L-sibirosaminide and its C-3 epimer are described using L-allothreonine as the chiral educt. Amino acylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-allothreonine constitute the key carbon-carbon bond-forming steps. The resulting methyl and vinyl ketones are then converted to tertiary alcohols by a second organometallic addition, and the order of addition controls the stereochemistry at the new chiral center. Stereocontrolled functionalization of the vinyl group then leads to the amino sugars. Elaboration to the C-3 epimer of sibirosamine was achieved via a Pummerer oxidation route, while in the preparation of sibirosamine itself a selective tetraol oxidation route was used.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>L-allothreonine</subject><subject>methyl L-sibirosaminide</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><recordid>eNptkMFu1DAQhiMEEkvhxAv4gOCAsoztxEmOVVQoUgVIFHG0Js5EcUni4MlK7JPwunjZquLAXCz9_uafmT_LXkrYS1Dy3V0AUKARoH6U7WSpIDcNFI-zXdJVrpXRT7NnzHeQqizLXfYbp3XEfX45-yUIdL5ngSzc6CNOgvqD21gMISbxOM-0Re_EGsNffS_ahAVeyfkh6XxctpGYWIRBJHY8TuImZ9-dIEwDfE8Cl1745NnmWtDqZ4piiGFOIE5T2MZIYfELPc-eDDgxvbh_L7Jv769u2-v85vOHj-1lorWRW14XVQ-yQD1A7TQ0Dfa1MqpvDHUdFJUzSlZUVyAb1XUlGodoetJ1T4S1BH2RvT77pqN-Hog3O3t2NE24UDiwlYUuyso0CXx7Bl06hiMNdo1-xni0EuwpfPtP-Il-dW-L7HAaIi7O80NLA1qDPpnmZ8zzRr8evjH-sKbSVWlvv3y1198_NaqVxpaJf3Pm0XGad4hLyua_C_wB8Q-hRg</recordid><startdate>19850201</startdate><enddate>19850201</enddate><creator>Maurer, Peter J</creator><creator>Knudsen, Christopher G</creator><creator>Palkowitz, Alan D</creator><creator>Rapoport, Henry</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>19850201</creationdate><title>alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine</title><author>Maurer, Peter J ; Knudsen, Christopher G ; Palkowitz, Alan D ; Rapoport, Henry</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a361t-847d014a3f08c3099ad8262d96ebb047c6217e870192bb5a6caa6de38deea8103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>L-allothreonine</topic><topic>methyl L-sibirosaminide</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maurer, Peter J</creatorcontrib><creatorcontrib>Knudsen, Christopher G</creatorcontrib><creatorcontrib>Palkowitz, Alan D</creatorcontrib><creatorcontrib>Rapoport, Henry</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maurer, Peter J</au><au>Knudsen, Christopher G</au><au>Palkowitz, Alan D</au><au>Rapoport, Henry</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1985-02-01</date><risdate>1985</risdate><volume>50</volume><issue>3</issue><spage>325</spage><epage>332</epage><pages>325-332</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Efficient syntheses of methyl L-sibirosaminide and its C-3 epimer are described using L-allothreonine as the chiral educt. Amino acylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-allothreonine constitute the key carbon-carbon bond-forming steps. The resulting methyl and vinyl ketones are then converted to tertiary alcohols by a second organometallic addition, and the order of addition controls the stereochemistry at the new chiral center. Stereocontrolled functionalization of the vinyl group then leads to the amino sugars. Elaboration to the C-3 epimer of sibirosamine was achieved via a Pummerer oxidation route, while in the preparation of sibirosamine itself a selective tetraol oxidation route was used.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jo00203a008</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 1985-02, Vol.50 (3), p.325-332 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Heterocyclic compounds L-allothreonine methyl L-sibirosaminide Organic chemistry Organic compounds Physics Preparations and properties Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine |
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