Commercial synthesis of α-D-cellobiosyl bromide heptaacetate
A detailed commercial process for the synthesis and purification of the activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination afford...
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| Veröffentlicht in: | Journal of chemical technology and biotechnology (1986) 1994-07, Vol.60 (3), p.253-256 |
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| container_issue | 3 |
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| container_title | Journal of chemical technology and biotechnology (1986) |
| container_volume | 60 |
| creator | Goggin, Katherine D. Hammen, Philip D. Kuntson, Kimberlee L. Lambert, Jack F. Walinsky, Stanley W. Watson Jr, Harry A. |
| description | A detailed commercial process for the synthesis and purification of the activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. alpha-D-Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant. |
| doi_str_mv | 10.1002/jctb.280600305 |
| format | Article |
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Reaction of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. alpha-D-Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.</description><identifier>ISSN: 0268-2575</identifier><identifier>EISSN: 1097-4660</identifier><identifier>DOI: 10.1002/jctb.280600305</identifier><identifier>PMID: 7764992</identifier><identifier>CODEN: JCTBDC</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Acetates - chemical synthesis ; Acetates - isolation & purification ; acetobromo-α-D-cellobiose ; Biological and medical sciences ; Biotechnology ; Carbohydrate Sequence ; Cellobiose - analogs & derivatives ; Cellobiose - chemical synthesis ; Chemical industry. Chemical engineering ; Chromatography, High Pressure Liquid ; Disaccharides - chemical synthesis ; Disaccharides - isolation & purification ; Filtration ; Fundamental and applied biological sciences. Psychology ; HBr bromination of α-cellobiose octaacetate ; Hydrobromic Acid ; Industrial applications and implications. Economical aspects ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Molecular Structure ; α-D-cellobiosyl bromide heptaacetate</subject><ispartof>Journal of chemical technology and biotechnology (1986), 1994-07, Vol.60 (3), p.253-256</ispartof><rights>1994 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-1a0a489cfcb27ab22cd17b753a6ca91da9478cece972a12ece6a617487a7adba3</citedby><cites>FETCH-LOGICAL-c357t-1a0a489cfcb27ab22cd17b753a6ca91da9478cece972a12ece6a617487a7adba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4172350$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7764992$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Goggin, Katherine D.</creatorcontrib><creatorcontrib>Hammen, Philip D.</creatorcontrib><creatorcontrib>Kuntson, Kimberlee L.</creatorcontrib><creatorcontrib>Lambert, Jack F.</creatorcontrib><creatorcontrib>Walinsky, Stanley W.</creatorcontrib><creatorcontrib>Watson Jr, Harry A.</creatorcontrib><title>Commercial synthesis of α-D-cellobiosyl bromide heptaacetate</title><title>Journal of chemical technology and biotechnology (1986)</title><addtitle>J. Chem. Technol. Biotechnol</addtitle><description>A detailed commercial process for the synthesis and purification of the activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. alpha-D-Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.</description><subject>Acetates - chemical synthesis</subject><subject>Acetates - isolation & purification</subject><subject>acetobromo-α-D-cellobiose</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Carbohydrate Sequence</subject><subject>Cellobiose - analogs & derivatives</subject><subject>Cellobiose - chemical synthesis</subject><subject>Chemical industry. Chemical engineering</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Disaccharides - chemical synthesis</subject><subject>Disaccharides - isolation & purification</subject><subject>Filtration</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HBr bromination of α-cellobiose octaacetate</subject><subject>Hydrobromic Acid</subject><subject>Industrial applications and implications. Economical aspects</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Sequence Data</subject><subject>Molecular Structure</subject><subject>α-D-cellobiosyl bromide heptaacetate</subject><issn>0268-2575</issn><issn>1097-4660</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kE1Lw0AQhhdRaq1evQk5iLfU3U2yszl4kKpVCH6A4nGZbDY0NWnq7hbsz_KP-JtMachpBt5nXoaHkHNGp4xSfr3UPp9ySQWlEU0OyJjRFMJYCHpIxpQLGfIEkmNy4tySUiokFyMyAhBxmvIxuZm1TWOsrrAO3HblF8ZVLmjL4O83vAu1qes2r1q3rYPctk1VmGBh1h5RG4_enJKjEmtnzvo5IR8P9--zxzB7mT_NbrNQRwn4kCHFWKa61DkHzDnXBYMckgiFxpQVmMYgtdEmBY6Md4tAwSCWgIBFjtGEXO1717b93hjnVVO53XO4Mu3GKRCJBCZFB073oLatc9aUam2rBu1WMap2vtTOlxp8dQcXffMmb0wx4L2gLr_sc3Qa69LiSlduwGIGPEpoh4V7rHLe_Awx2i8lIIJEfT7PFX_LWCaZUK_RP_fVg2Y</recordid><startdate>19940701</startdate><enddate>19940701</enddate><creator>Goggin, Katherine D.</creator><creator>Hammen, Philip D.</creator><creator>Kuntson, Kimberlee L.</creator><creator>Lambert, Jack F.</creator><creator>Walinsky, Stanley W.</creator><creator>Watson Jr, Harry A.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</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>19940701</creationdate><title>Commercial synthesis of α-D-cellobiosyl bromide heptaacetate</title><author>Goggin, Katherine D. ; Hammen, Philip D. ; Kuntson, Kimberlee L. ; Lambert, Jack F. ; Walinsky, Stanley W. ; Watson Jr, Harry A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-1a0a489cfcb27ab22cd17b753a6ca91da9478cece972a12ece6a617487a7adba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Acetates - chemical synthesis</topic><topic>Acetates - isolation & purification</topic><topic>acetobromo-α-D-cellobiose</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Carbohydrate Sequence</topic><topic>Cellobiose - analogs & derivatives</topic><topic>Cellobiose - chemical synthesis</topic><topic>Chemical industry. Chemical engineering</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Disaccharides - chemical synthesis</topic><topic>Disaccharides - isolation & purification</topic><topic>Filtration</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HBr bromination of α-cellobiose octaacetate</topic><topic>Hydrobromic Acid</topic><topic>Industrial applications and implications. Economical aspects</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Sequence Data</topic><topic>Molecular Structure</topic><topic>α-D-cellobiosyl bromide heptaacetate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goggin, Katherine D.</creatorcontrib><creatorcontrib>Hammen, Philip D.</creatorcontrib><creatorcontrib>Kuntson, Kimberlee L.</creatorcontrib><creatorcontrib>Lambert, Jack F.</creatorcontrib><creatorcontrib>Walinsky, Stanley W.</creatorcontrib><creatorcontrib>Watson Jr, Harry A.</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 chemical technology and biotechnology (1986)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goggin, Katherine D.</au><au>Hammen, Philip D.</au><au>Kuntson, Kimberlee L.</au><au>Lambert, Jack F.</au><au>Walinsky, Stanley W.</au><au>Watson Jr, Harry A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Commercial synthesis of α-D-cellobiosyl bromide heptaacetate</atitle><jtitle>Journal of chemical technology and biotechnology (1986)</jtitle><addtitle>J. Chem. Technol. Biotechnol</addtitle><date>1994-07-01</date><risdate>1994</risdate><volume>60</volume><issue>3</issue><spage>253</spage><epage>256</epage><pages>253-256</pages><issn>0268-2575</issn><eissn>1097-4660</eissn><coden>JCTBDC</coden><abstract>A detailed commercial process for the synthesis and purification of the activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. alpha-D-Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>7764992</pmid><doi>10.1002/jctb.280600305</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0268-2575 |
| ispartof | Journal of chemical technology and biotechnology (1986), 1994-07, Vol.60 (3), p.253-256 |
| issn | 0268-2575 1097-4660 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Acetates - chemical synthesis Acetates - isolation & purification acetobromo-α-D-cellobiose Biological and medical sciences Biotechnology Carbohydrate Sequence Cellobiose - analogs & derivatives Cellobiose - chemical synthesis Chemical industry. Chemical engineering Chromatography, High Pressure Liquid Disaccharides - chemical synthesis Disaccharides - isolation & purification Filtration Fundamental and applied biological sciences. Psychology HBr bromination of α-cellobiose octaacetate Hydrobromic Acid Industrial applications and implications. Economical aspects Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure α-D-cellobiosyl bromide heptaacetate |
| title | Commercial synthesis of α-D-cellobiosyl bromide heptaacetate |
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