Synthesis, structure and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside
The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D- galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-beta-D- tagatofuranos...
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| Veröffentlicht in: | Journal of carbohydrate chemistry 1999, Vol.18 (2), p.241-253 |
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| container_title | Journal of carbohydrate chemistry |
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| creator | Lee, C.K Kang, H.C Linden, A |
| description | The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D- galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-beta-D- tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4' is discussed. The intensity of sweetness of the free 4'-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic gamma-site is located at C-4'. |
| doi_str_mv | 10.1080/07328309908543993 |
| format | Article |
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The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D- galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-beta-D- tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4' is discussed. The intensity of sweetness of the free 4'-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic gamma-site is located at C-4'.</description><identifier>ISSN: 0732-8303</identifier><identifier>EISSN: 1532-2327</identifier><identifier>DOI: 10.1080/07328309908543993</identifier><language>eng</language><publisher>Taylor & Francis Group</publisher><subject>chemical structure ; sweet-tasting compounds</subject><ispartof>Journal of carbohydrate chemistry, 1999, Vol.18 (2), p.241-253</ispartof><rights>Copyright Taylor & Francis Group, LLC 1999</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-c23122ebed5ea463d68185e84242aba198227c6cde2e94208f642ec44fff88993</citedby><cites>FETCH-LOGICAL-c368t-c23122ebed5ea463d68185e84242aba198227c6cde2e94208f642ec44fff88993</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/07328309908543993$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/07328309908543993$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,776,780,4010,27900,27901,27902,59620,60409</link.rule.ids></links><search><creatorcontrib>Lee, C.K</creatorcontrib><creatorcontrib>Kang, H.C</creatorcontrib><creatorcontrib>Linden, A</creatorcontrib><title>Synthesis, structure and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside</title><title>Journal of carbohydrate chemistry</title><description>The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D- galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-beta-D- tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4' is discussed. The intensity of sweetness of the free 4'-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic gamma-site is located at C-4'.</description><subject>chemical structure</subject><subject>sweet-tasting compounds</subject><issn>0732-8303</issn><issn>1532-2327</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNqF0M1KxDAQB_AgCq4fD-DJPsBGk0naJuBF_AbBg3ous2myW6nNkmTZ7Qv43HateBH0NAwzv4H5E3LC2Rlnip2zUoASTGumcim0FjtkwnMBFASUu2SyndNhQeyTgxjfGGNQ5nxCPp77Li1sbOI0iymsTFoFm2FXZ3FtbepsjJl3maRm0frgqaS19ZueYrtcIL2mc2zRJL_sA3Y-9m3Gp3Ja0BSab_DTj25m05YlnGPybvWlhtER2XPYRnv8XQ_J6-3Ny9U9fXy6e7i6fKRGFCpRA4ID2Jmtc4uyEHWhuMqtkiABZ8i1AihNYWoLVktgyhUSrJHSOafUkMoh4eNdE3yMwbpqGZp3DH3FWbUNsvoV5GAuRtN0zod3XPvQ1lXCfvjPDQ-YJlbiL17-y3-pKm3SIE9H6dBXOA_D4uszMC4YaCa0FOITltOVkg</recordid><startdate>1999</startdate><enddate>1999</enddate><creator>Lee, C.K</creator><creator>Kang, H.C</creator><creator>Linden, A</creator><general>Taylor & Francis Group</general><scope>FBQ</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>1999</creationdate><title>Synthesis, structure and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside</title><author>Lee, C.K ; Kang, H.C ; Linden, A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-c23122ebed5ea463d68185e84242aba198227c6cde2e94208f642ec44fff88993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>chemical structure</topic><topic>sweet-tasting compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, C.K</creatorcontrib><creatorcontrib>Kang, H.C</creatorcontrib><creatorcontrib>Linden, A</creatorcontrib><collection>AGRIS</collection><collection>CrossRef</collection><jtitle>Journal of carbohydrate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, C.K</au><au>Kang, H.C</au><au>Linden, A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structure and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside</atitle><jtitle>Journal of carbohydrate chemistry</jtitle><date>1999</date><risdate>1999</risdate><volume>18</volume><issue>2</issue><spage>241</spage><epage>253</epage><pages>241-253</pages><issn>0732-8303</issn><eissn>1532-2327</eissn><abstract>The reaction of 6-O-acetylsucrose with sulfuryl chloride was reexamined. The major product, after dechlorosulfation and acetylation, was determined by X-ray diffraction to be 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D- galactopyranosyl 3-O-acetyl-1,4,6-trichloro-1,4,6-trideoxy-beta-D- tagatofuranoside and not the corresponding sorbofuranoside, as reported earlier. The mechanism of chlorination at C-4' is discussed. The intensity of sweetness of the free 4'-chlorodeoxy tagato isomer is determined to be only about one-tenth the sweetness of the corresponding chlorodeoxy fructo isomer, which strongly suggests that the hydrophobic gamma-site is located at C-4'.</abstract><pub>Taylor & Francis Group</pub><doi>10.1080/07328309908543993</doi><tpages>13</tpages></addata></record> |
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| ispartof | Journal of carbohydrate chemistry, 1999, Vol.18 (2), p.241-253 |
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| language | eng |
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| source | Taylor & Francis Journals Complete |
| subjects | chemical structure sweet-tasting compounds |
| title | Synthesis, structure and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside |
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