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Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation
Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent...
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Published in: | Bulletin of the Chemical Society of Japan 2002, Vol.75 (6), p.1301-1309 |
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container_title | Bulletin of the Chemical Society of Japan |
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creator | Hirooka, Motoko Terayama, Megumi Mitani, Emi Koto, Shinkiti Miura, Asako Chiba, Kayo Takabatake, Ayano Tashiro, Takako |
description | Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful. |
doi_str_mv | 10.1246/bcsj.75.1301 |
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The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.</description><identifier>ISSN: 0009-2673</identifier><identifier>EISSN: 1348-0634</identifier><identifier>DOI: 10.1246/bcsj.75.1301</identifier><language>eng</language><publisher>The Chemical Society of Japan</publisher><ispartof>Bulletin of the Chemical Society of Japan, 2002, Vol.75 (6), p.1301-1309</ispartof><rights>The Chemical Society of Japan</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Hirooka, Motoko</creatorcontrib><creatorcontrib>Terayama, Megumi</creatorcontrib><creatorcontrib>Mitani, Emi</creatorcontrib><creatorcontrib>Koto, Shinkiti</creatorcontrib><creatorcontrib>Miura, Asako</creatorcontrib><creatorcontrib>Chiba, Kayo</creatorcontrib><creatorcontrib>Takabatake, Ayano</creatorcontrib><creatorcontrib>Tashiro, Takako</creatorcontrib><title>Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation</title><title>Bulletin of the Chemical Society of Japan</title><addtitle>Bulletin of the Chemical Society of Japan</addtitle><description>Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.</description><issn>0009-2673</issn><issn>1348-0634</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNpdkE1Kw0AYhgdRsFZ3HmCWLXTq_CdZuJBWq9DShboSCdPJF5KQTqQTC7mAB3DvIbyIh_AkJra4cPXxfjy8LzwInTM6Zlzqi5X1xThQYyYoO0A9JmRIqBbyEPUopRHhOhDH6MT7oo2hklEPfdw3rs7A5x5XKV5AnTUlXpKvTzIlC-Nc5ZuSDNj327sckqeBIEuy_oV2CF7vmeEf9Oz-QzsmT8DjgcOXmI4wG2HjEsyHeJsbPIWsSTamzreAZ2Vju8I2Ve4UHaWm9HC2v330eHP9MLkl8-XsbnI1J5aHqiZ8FYWJFAxSlYZKaA4GuKTWWpBMK8MDrZlgZmU4tYpbUFonTIKMIk0NgOijaNdrM1jntp2qbA51U5gX4-Kiet249hczGnee485zHKi48yx-AMO-cwY</recordid><startdate>2002</startdate><enddate>2002</enddate><creator>Hirooka, Motoko</creator><creator>Terayama, Megumi</creator><creator>Mitani, Emi</creator><creator>Koto, Shinkiti</creator><creator>Miura, Asako</creator><creator>Chiba, Kayo</creator><creator>Takabatake, Ayano</creator><creator>Tashiro, Takako</creator><general>The Chemical Society of Japan</general><scope/></search><sort><creationdate>2002</creationdate><title>Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation</title><author>Hirooka, Motoko ; Terayama, Megumi ; Mitani, Emi ; Koto, Shinkiti ; Miura, Asako ; Chiba, Kayo ; Takabatake, Ayano ; Tashiro, Takako</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c285t-2b98d431ef5f85362eae240ccce4165a2766131aba20c52ce566d14e49960aee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hirooka, Motoko</creatorcontrib><creatorcontrib>Terayama, Megumi</creatorcontrib><creatorcontrib>Mitani, Emi</creatorcontrib><creatorcontrib>Koto, Shinkiti</creatorcontrib><creatorcontrib>Miura, Asako</creatorcontrib><creatorcontrib>Chiba, Kayo</creatorcontrib><creatorcontrib>Takabatake, Ayano</creatorcontrib><creatorcontrib>Tashiro, Takako</creatorcontrib><jtitle>Bulletin of the Chemical Society of Japan</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hirooka, Motoko</au><au>Terayama, Megumi</au><au>Mitani, Emi</au><au>Koto, Shinkiti</au><au>Miura, Asako</au><au>Chiba, Kayo</au><au>Takabatake, Ayano</au><au>Tashiro, Takako</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation</atitle><jtitle>Bulletin of the Chemical Society of Japan</jtitle><addtitle>Bulletin of the Chemical Society of Japan</addtitle><date>2002</date><risdate>2002</risdate><volume>75</volume><issue>6</issue><spage>1301</spage><epage>1309</epage><pages>1301-1309</pages><issn>0009-2673</issn><eissn>1348-0634</eissn><abstract>Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.</abstract><pub>The Chemical Society of Japan</pub><doi>10.1246/bcsj.75.1301</doi><tpages>9</tpages></addata></record> |
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title | Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation |
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