The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin
The synthesis of 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-1,2,5-trideoxy-1,5-imino- d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected N-benzyl-1,5-dideoxy-1,5-imino-4,6- O-isopropylidene- d-mannitol,...
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| Veröffentlicht in: | Carbohydrate research 1987-07, Vol.164, p.141-148 |
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| container_title | Carbohydrate research |
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| creator | Böshagen, Horst Heiker, Fred-Robert Matthias Schüller, A. |
| description | The synthesis of 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-1,2,5-trideoxy-1,5-imino-
d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected
N-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-
d-mannitol, the triflate ester
N-benzyl-3-
O-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-2-
O-(trifluoromethylsulfonyl)-
d-mannitol, and 2-azido-
N-benzyl-3-
O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-
O-isopropylidene-
d-glucitol, readily obtained in a sequence from 1-deoxynojirimycin. Thus 1-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry. |
| doi_str_mv | 10.1016/0008-6215(87)80126-X |
| format | Article |
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d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected
N-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-
d-mannitol, the triflate ester
N-benzyl-3-
O-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-2-
O-(trifluoromethylsulfonyl)-
d-mannitol, and 2-azido-
N-benzyl-3-
O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-
O-isopropylidene-
d-glucitol, readily obtained in a sequence from 1-deoxynojirimycin. Thus 1-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/0008-6215(87)80126-X</identifier><identifier>PMID: 2957054</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>1-Deoxynojirimycin ; Antibodies ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Exact sciences and technology ; Glucosamine - analogs & derivatives ; Glucosamine - chemical synthesis ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Optical Rotation ; Organic chemistry ; Preparations and properties</subject><ispartof>Carbohydrate research, 1987-07, Vol.164, p.141-148</ispartof><rights>1987</rights><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-85956c6e5fd2ff53516fe7205c864e5a8037528c199357210d22c9ed109b583c3</citedby><cites>FETCH-LOGICAL-c367t-85956c6e5fd2ff53516fe7205c864e5a8037528c199357210d22c9ed109b583c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0008-6215(87)80126-X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8222978$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2957054$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Böshagen, Horst</creatorcontrib><creatorcontrib>Heiker, Fred-Robert</creatorcontrib><creatorcontrib>Matthias Schüller, A.</creatorcontrib><title>The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>The synthesis of 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-1,2,5-trideoxy-1,5-imino-
d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected
N-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-
d-mannitol, the triflate ester
N-benzyl-3-
O-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-2-
O-(trifluoromethylsulfonyl)-
d-mannitol, and 2-azido-
N-benzyl-3-
O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-
O-isopropylidene-
d-glucitol, readily obtained in a sequence from 1-deoxynojirimycin. Thus 1-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry.</description><subject>1-Deoxynojirimycin</subject><subject>Antibodies</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Glucosamine - analogs & derivatives</subject><subject>Glucosamine - chemical synthesis</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Optical Rotation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LHDEUhoNYdN32H1iYCykWjE0yk4-5KRSxKgheaGHvQkxO2Cw7kzWZtZ1_36y77E2lVyE5z_ty8iB0SsklJVR8I4QoLBjl50p-VYQygWcHaEKVrHHDxOwQTfbIMTrJeVGuREhxhI5YyyXhzQT9fppDZefQhTyksYq-GsoDxQ7in7GPi5BCN9rQV3nMA3SX1ePYFyKHvGEZNhYG0wUXMb1g2IV_cj7F7p2-j-iDN8sMn3bnFP36ef10dYvvH27urn7cY1sLOWDFWy6sAO4d857XnAoPkhFulWiAG0VqyZmytG1rLhkljjHbgqOkfeaqtvUUfdn2rlJ8WUMedPmpheXS9BDXWUspeEOkKGCzBW2KOSfwelVWNWnUlOiNb72RqTcytZL6zbeeldjnXf_6uQO3D-0El_nZbm6yNUufTG9D3mOKMdZKVbDvWwyKi9cASWcboLfgQgI7aBfD__f4C4AZnK4</recordid><startdate>19870701</startdate><enddate>19870701</enddate><creator>Böshagen, Horst</creator><creator>Heiker, Fred-Robert</creator><creator>Matthias Schüller, A.</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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>19870701</creationdate><title>The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin</title><author>Böshagen, Horst ; Heiker, Fred-Robert ; Matthias Schüller, A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-85956c6e5fd2ff53516fe7205c864e5a8037528c199357210d22c9ed109b583c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>1-Deoxynojirimycin</topic><topic>Antibodies</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Glucosamine - analogs & derivatives</topic><topic>Glucosamine - chemical synthesis</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Optical Rotation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Böshagen, Horst</creatorcontrib><creatorcontrib>Heiker, Fred-Robert</creatorcontrib><creatorcontrib>Matthias Schüller, A.</creatorcontrib><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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Böshagen, Horst</au><au>Heiker, Fred-Robert</au><au>Matthias Schüller, A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1987-07-01</date><risdate>1987</risdate><volume>164</volume><spage>141</spage><epage>148</epage><pages>141-148</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>The synthesis of 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-1,2,5-trideoxy-1,5-imino-
d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected
N-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-
d-mannitol, the triflate ester
N-benzyl-3-
O-benzyl-1,5-dideoxy-1,5-imino-4,6-
O-isopropylidene-2-
O-(trifluoromethylsulfonyl)-
d-mannitol, and 2-azido-
N-benzyl-3-
O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-
O-isopropylidene-
d-glucitol, readily obtained in a sequence from 1-deoxynojirimycin. Thus 1-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>2957054</pmid><doi>10.1016/0008-6215(87)80126-X</doi><tpages>8</tpages></addata></record> |
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| ispartof | Carbohydrate research, 1987-07, Vol.164, p.141-148 |
| issn | 0008-6215 1873-426X |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 1-Deoxynojirimycin Antibodies Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Glucosamine - analogs & derivatives Glucosamine - chemical synthesis Indicators and Reagents Magnetic Resonance Spectroscopy Optical Rotation Organic chemistry Preparations and properties |
| title | The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin |
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