Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
An efficient glycosylation reaction of 5-thioglucopyranose was developed and was applied for the preparation of oligosaccharides composed of 5-thioglucopyranose units. Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2- O-position 14– 15...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2005-09, Vol.13 (17), p.5113-5144 |
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| container_issue | 17 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Morii, Yasuharu Matsuda, Hiroko Ohara, Keiichiro Hashimoto, Masaru Miyairi, Kazuo Okuno, Toshikatsu |
| description | An efficient glycosylation reaction of 5-thioglucopyranose was developed and was applied for the preparation of oligosaccharides composed of 5-thioglucopyranose units.
Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-
O-position
14–
15, and
37 proceed smoothly to give α-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside
2 and maltotetraoside
3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate
12 underwent β-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF
3OEt
2. This was applied for preparation of sulfur-substituted gentiobiosides
1 and
46. |
| doi_str_mv | 10.1016/j.bmc.2005.05.028 |
| format | Article |
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Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-
O-position
14–
15, and
37 proceed smoothly to give α-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside
2 and maltotetraoside
3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate
12 underwent β-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF
3OEt
2. This was applied for preparation of sulfur-substituted gentiobiosides
1 and
46.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.05.028</identifier><identifier>PMID: 15982892</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>5-Thioglucopyranosyl trichloroacetimidates ; Carbohydrate Sequence ; endo-Glycosidases ; Glycosylation ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Oligosaccharides - chemical synthesis ; Oligosaccharides - chemistry ; Spectrometry, Mass, Fast Atom Bombardment ; Thioglucosides - chemical synthesis ; Thioglucosides - chemistry ; α-selective glycosylation ; β-selective glycosylation</subject><ispartof>Bioorganic & medicinal chemistry, 2005-09, Vol.13 (17), p.5113-5144</ispartof><rights>2005 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-6200cc3d5dc26aa171c24eb2b0ee7da39a75a0c1233b69fe5c801b3c43a77af3</citedby><cites>FETCH-LOGICAL-c417t-6200cc3d5dc26aa171c24eb2b0ee7da39a75a0c1233b69fe5c801b3c43a77af3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2005.05.028$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15982892$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morii, Yasuharu</creatorcontrib><creatorcontrib>Matsuda, Hiroko</creatorcontrib><creatorcontrib>Ohara, Keiichiro</creatorcontrib><creatorcontrib>Hashimoto, Masaru</creatorcontrib><creatorcontrib>Miyairi, Kazuo</creatorcontrib><creatorcontrib>Okuno, Toshikatsu</creatorcontrib><title>Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>An efficient glycosylation reaction of 5-thioglucopyranose was developed and was applied for the preparation of oligosaccharides composed of 5-thioglucopyranose units.
Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-
O-position
14–
15, and
37 proceed smoothly to give α-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside
2 and maltotetraoside
3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate
12 underwent β-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF
3OEt
2. This was applied for preparation of sulfur-substituted gentiobiosides
1 and
46.</description><subject>5-Thioglucopyranosyl trichloroacetimidates</subject><subject>Carbohydrate Sequence</subject><subject>endo-Glycosidases</subject><subject>Glycosylation</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Sequence Data</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Thioglucosides - chemical synthesis</subject><subject>Thioglucosides - chemistry</subject><subject>α-selective glycosylation</subject><subject>β-selective glycosylation</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1Lw0AQxRdRbK3-AV4kJ2-p-5FsNniS4hcWPNj7spmdtFuSbN1NhP73prTgTRgYeLz3mPkRcsvonFEmH7bzqoU5pzSfH4arMzJlmcxSIUp2Tqa0lCqlqpQTchXjllLKs5JdkgnLS8VVyafk42vf9RvsHSSxH6zDmPgu8Y1b-2gANiY4O2rg252PaBNfJ3nab5xfNwP43T6YbtSToXN9vCYXtWki3pz2jKxenleLt3T5-fq-eFqmkLGiT-V4MICwuQUujWEFA55hxSuKWFgjSlPkhgLjQlSyrDEHRVklIBOmKEwtZuT-WLsL_nvA2OvWRcCmMR36IWqpqJJFxkYjOxoh-BgD1noXXGvCXjOqDwD1Vo8A9QGgPgxXY-buVD5ULdq_xInYaHg8GnD88Mdh0BEcdoDWBYReW-_-qf8F9_-CRg</recordid><startdate>20050901</startdate><enddate>20050901</enddate><creator>Morii, Yasuharu</creator><creator>Matsuda, Hiroko</creator><creator>Ohara, Keiichiro</creator><creator>Hashimoto, Masaru</creator><creator>Miyairi, Kazuo</creator><creator>Okuno, Toshikatsu</creator><general>Elsevier Ltd</general><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>20050901</creationdate><title>Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units</title><author>Morii, Yasuharu ; Matsuda, Hiroko ; Ohara, Keiichiro ; Hashimoto, Masaru ; Miyairi, Kazuo ; Okuno, Toshikatsu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-6200cc3d5dc26aa171c24eb2b0ee7da39a75a0c1233b69fe5c801b3c43a77af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>5-Thioglucopyranosyl trichloroacetimidates</topic><topic>Carbohydrate Sequence</topic><topic>endo-Glycosidases</topic><topic>Glycosylation</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Sequence Data</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Thioglucosides - chemical synthesis</topic><topic>Thioglucosides - chemistry</topic><topic>α-selective glycosylation</topic><topic>β-selective glycosylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morii, Yasuharu</creatorcontrib><creatorcontrib>Matsuda, Hiroko</creatorcontrib><creatorcontrib>Ohara, Keiichiro</creatorcontrib><creatorcontrib>Hashimoto, Masaru</creatorcontrib><creatorcontrib>Miyairi, Kazuo</creatorcontrib><creatorcontrib>Okuno, Toshikatsu</creatorcontrib><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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morii, Yasuharu</au><au>Matsuda, Hiroko</au><au>Ohara, Keiichiro</au><au>Hashimoto, Masaru</au><au>Miyairi, Kazuo</au><au>Okuno, Toshikatsu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2005-09-01</date><risdate>2005</risdate><volume>13</volume><issue>17</issue><spage>5113</spage><epage>5144</epage><pages>5113-5144</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>An efficient glycosylation reaction of 5-thioglucopyranose was developed and was applied for the preparation of oligosaccharides composed of 5-thioglucopyranose units.
Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-
O-position
14–
15, and
37 proceed smoothly to give α-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside
2 and maltotetraoside
3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate
12 underwent β-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF
3OEt
2. This was applied for preparation of sulfur-substituted gentiobiosides
1 and
46.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>15982892</pmid><doi>10.1016/j.bmc.2005.05.028</doi><tpages>32</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2005-09, Vol.13 (17), p.5113-5144 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 5-Thioglucopyranosyl trichloroacetimidates Carbohydrate Sequence endo-Glycosidases Glycosylation Magnetic Resonance Spectroscopy Molecular Sequence Data Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Spectrometry, Mass, Fast Atom Bombardment Thioglucosides - chemical synthesis Thioglucosides - chemistry α-selective glycosylation β-selective glycosylation |
| title | Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units |
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