Synthesis of β- l-fucopyranosyl phosphate and l-fucofuranosyl phosphates by the MacDonald procedure
Fusion or β- l-fucopyranose tetraacetate with phosphoric acid for 1 min at 50° gives a 9:1 anomeric mixture of the α-and β-pyranosyl phosphates. Longer fusion times give the α-anomer exclusively. The l-fucofuranose tetraacetates were synthesized for the first time by acetolysis or methyl-2,3,5-tri-...
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| Veröffentlicht in: | Carbohydrate research 1977-07, Vol.56 (2), p.315-324 |
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| container_title | Carbohydrate research |
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| creator | Prihar, Harry S. Ji-Hsiung, Tsai Wanamaker, Steven R. Duber, Stephanie J. Bethrman, Edward J. |
| description | Fusion or β-
l-fucopyranose tetraacetate with phosphoric acid for 1 min at 50° gives a 9:1 anomeric mixture of the α-and β-pyranosyl phosphates. Longer fusion times give the α-anomer exclusively. The
l-fucofuranose tetraacetates were synthesized for the first time by acetolysis or methyl-2,3,5-tri-
O-acetyl-β-
l-fucofuranoside. Fusion or the furanose tetraacetates with phosphoric acid gave a mixture or the fucofuranosyl phosphates in which the β-anomer predominated (β/α = 2.4). Anomeric pairs in the fucofuranose series appear to be distinguishable by the chemical shift of the C-6 methyl protons, as already shown by Sinclair and Sleeter in the pyranose series. |
| doi_str_mv | 10.1016/S0008-6215(00)83352-2 |
| format | Article |
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l-fucopyranose tetraacetate with phosphoric acid for 1 min at 50° gives a 9:1 anomeric mixture of the α-and β-pyranosyl phosphates. Longer fusion times give the α-anomer exclusively. The
l-fucofuranose tetraacetates were synthesized for the first time by acetolysis or methyl-2,3,5-tri-
O-acetyl-β-
l-fucofuranoside. Fusion or the furanose tetraacetates with phosphoric acid gave a mixture or the fucofuranosyl phosphates in which the β-anomer predominated (β/α = 2.4). Anomeric pairs in the fucofuranose series appear to be distinguishable by the chemical shift of the C-6 methyl protons, as already shown by Sinclair and Sleeter in the pyranose series.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/S0008-6215(00)83352-2</identifier><identifier>PMID: 902265</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Fucose ; Glycosides ; Hexosephosphates - chemical synthesis ; Isomerism ; Magnetic Resonance Spectroscopy ; Methods ; Molecular Conformation</subject><ispartof>Carbohydrate research, 1977-07, Vol.56 (2), p.315-324</ispartof><rights>1977</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0008-6215(00)83352-2$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/902265$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Prihar, Harry S.</creatorcontrib><creatorcontrib>Ji-Hsiung, Tsai</creatorcontrib><creatorcontrib>Wanamaker, Steven R.</creatorcontrib><creatorcontrib>Duber, Stephanie J.</creatorcontrib><creatorcontrib>Bethrman, Edward J.</creatorcontrib><title>Synthesis of β- l-fucopyranosyl phosphate and l-fucofuranosyl phosphates by the MacDonald procedure</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Fusion or β-
l-fucopyranose tetraacetate with phosphoric acid for 1 min at 50° gives a 9:1 anomeric mixture of the α-and β-pyranosyl phosphates. Longer fusion times give the α-anomer exclusively. The
l-fucofuranose tetraacetates were synthesized for the first time by acetolysis or methyl-2,3,5-tri-
O-acetyl-β-
l-fucofuranoside. Fusion or the furanose tetraacetates with phosphoric acid gave a mixture or the fucofuranosyl phosphates in which the β-anomer predominated (β/α = 2.4). Anomeric pairs in the fucofuranose series appear to be distinguishable by the chemical shift of the C-6 methyl protons, as already shown by Sinclair and Sleeter in the pyranose series.</description><subject>Fucose</subject><subject>Glycosides</subject><subject>Hexosephosphates - chemical synthesis</subject><subject>Isomerism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Methods</subject><subject>Molecular Conformation</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1977</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplUctOwzAQtBCvUvgDkHxCcDDYTuLYJ4TKUyriUJC4WVs_1KA0CXGClN_iQ_gmXFpxYS-r1Yx2d2YQOmH0glEmLmeUUkkEZ9kZpecySTJO-BYaMZknJOXibRuN_ij76CCE9zhSkYs9tKso5yIbITsbqm7hQhFw7fH3F8El8b2pm6GFqg5DiZtFHZoFdA5DZTeo7_-hAc8HHDfhJzA3dQWlxU1bG2f71h2iHQ9lcEebPkavd7cvkwcyfb5_nFxPiWMq6YjPDQPBUpd5LxhknNq5MFKZ3PPUAwXJFOQ85yJVCmSsxCqAeZSXyVSwZIxO13vj5Y_ehU4vi2BcWULl6j5omVKlRJZH4vGG2M-XzuqmLZbQDnrtSoSv1rCLz34WrtXBFK6KYorWmU7butCM6lUK-jcFvbJYU6p_U9A8-QFo-nqn</recordid><startdate>197707</startdate><enddate>197707</enddate><creator>Prihar, Harry S.</creator><creator>Ji-Hsiung, Tsai</creator><creator>Wanamaker, Steven R.</creator><creator>Duber, Stephanie J.</creator><creator>Bethrman, Edward J.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>197707</creationdate><title>Synthesis of β- l-fucopyranosyl phosphate and l-fucofuranosyl phosphates by the MacDonald procedure</title><author>Prihar, Harry S. ; Ji-Hsiung, Tsai ; Wanamaker, Steven R. ; Duber, Stephanie J. ; Bethrman, Edward J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-e193t-f7c1a614e5ff61a520db6c89c7f24fa0a819a72726499a88883d9aab215584613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1977</creationdate><topic>Fucose</topic><topic>Glycosides</topic><topic>Hexosephosphates - chemical synthesis</topic><topic>Isomerism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Methods</topic><topic>Molecular Conformation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Prihar, Harry S.</creatorcontrib><creatorcontrib>Ji-Hsiung, Tsai</creatorcontrib><creatorcontrib>Wanamaker, Steven R.</creatorcontrib><creatorcontrib>Duber, Stephanie J.</creatorcontrib><creatorcontrib>Bethrman, Edward J.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Prihar, Harry S.</au><au>Ji-Hsiung, Tsai</au><au>Wanamaker, Steven R.</au><au>Duber, Stephanie J.</au><au>Bethrman, Edward J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of β- l-fucopyranosyl phosphate and l-fucofuranosyl phosphates by the MacDonald procedure</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1977-07</date><risdate>1977</risdate><volume>56</volume><issue>2</issue><spage>315</spage><epage>324</epage><pages>315-324</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Fusion or β-
l-fucopyranose tetraacetate with phosphoric acid for 1 min at 50° gives a 9:1 anomeric mixture of the α-and β-pyranosyl phosphates. Longer fusion times give the α-anomer exclusively. The
l-fucofuranose tetraacetates were synthesized for the first time by acetolysis or methyl-2,3,5-tri-
O-acetyl-β-
l-fucofuranoside. Fusion or the furanose tetraacetates with phosphoric acid gave a mixture or the fucofuranosyl phosphates in which the β-anomer predominated (β/α = 2.4). Anomeric pairs in the fucofuranose series appear to be distinguishable by the chemical shift of the C-6 methyl protons, as already shown by Sinclair and Sleeter in the pyranose series.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>902265</pmid><doi>10.1016/S0008-6215(00)83352-2</doi><tpages>10</tpages></addata></record> |
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| ispartof | Carbohydrate research, 1977-07, Vol.56 (2), p.315-324 |
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| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Fucose Glycosides Hexosephosphates - chemical synthesis Isomerism Magnetic Resonance Spectroscopy Methods Molecular Conformation |
| title | Synthesis of β- l-fucopyranosyl phosphate and l-fucofuranosyl phosphates by the MacDonald procedure |
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