Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g
The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4′-thioribonucleoside and altritol nucleoside. The desired compound, i.e. , 1-[(3 R ,4 R ,5 S ,6 R )-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil ( 20 ), was prepared via the Pummerer-like reaction, followed...
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| creator | Miyazawa, Tadashi Umezaki, Kouhei Tarashima, Noriko Furukawa, Kazuhiro Ooi, Takashi Minakawa, Noriaki |
| description | The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4′-thioribonucleoside and altritol nucleoside. The desired compound,
i.e.
, 1-[(3
R
,4
R
,5
S
,6
R
)-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil (
20
), was prepared
via
the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil.
The novel 1,2-dithianenucleoside was synthesized
via
Pummerer-like reaction followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil. |
| doi_str_mv | 10.1039/c3cc44848g |
| format | Article |
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i.e.
, 1-[(3
R
,4
R
,5
S
,6
R
)-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil (
20
), was prepared
via
the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil.
The novel 1,2-dithianenucleoside was synthesized
via
Pummerer-like reaction followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c3cc44848g</identifier><language>eng</language><creationdate>2013-08</creationdate><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>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Miyazawa, Tadashi</creatorcontrib><creatorcontrib>Umezaki, Kouhei</creatorcontrib><creatorcontrib>Tarashima, Noriko</creatorcontrib><creatorcontrib>Furukawa, Kazuhiro</creatorcontrib><creatorcontrib>Ooi, Takashi</creatorcontrib><creatorcontrib>Minakawa, Noriaki</creatorcontrib><title>Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g</title><description>The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4′-thioribonucleoside and altritol nucleoside. The desired compound,
i.e.
, 1-[(3
R
,4
R
,5
S
,6
R
)-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil (
20
), was prepared
via
the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil.
The novel 1,2-dithianenucleoside was synthesized
via
Pummerer-like reaction followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.</description><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkUFP3DAQhVPUSoXSC_dKw41KZNk0Cd3lGnbVPbUSCHFbzdqTrGFiR-MkS7j2j2N2KyGEVHyxNe_5mzd2FB0l41EyTqdnKlUqyybZpNqL9pP0PIvzbHL78fmcT-OfaZZ_jg68vxuHleST_Q9_rwbbrskbD64EBOt6YkhOf8TatGuDlmynmJw3mqA3CH-6uiYhidncEwihao2zp1A6ZrchDasBbpyspKsqslDxoJwfGJ9dsKJ2Q6GKrzqAJjF9cPQEaDV0gsrwjEm14qxR4LumYarJtigDGFs6qXfAk9nV4jtgj4ZxxXQBs4cmwLZWhkacIt0J-S1XrTGQ26A_7m5rbHE7NjNY2oBydeM6q_0IiuKygGmanOfjEcydQGi0g8jgA5tdJdisQ7gtxFgoFnMIPhdeU4Bewu_CgieCy9-LC3j7VYfRpxLZ09d_-5fo23x2XfyKxatlE6YJUy9f7On7-vH_9GWjy_QJorS4PQ</recordid><startdate>20130808</startdate><enddate>20130808</enddate><creator>Miyazawa, Tadashi</creator><creator>Umezaki, Kouhei</creator><creator>Tarashima, Noriko</creator><creator>Furukawa, Kazuhiro</creator><creator>Ooi, Takashi</creator><creator>Minakawa, Noriaki</creator><scope/></search><sort><creationdate>20130808</creationdate><title>Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g</title><author>Miyazawa, Tadashi ; Umezaki, Kouhei ; Tarashima, Noriko ; Furukawa, Kazuhiro ; Ooi, Takashi ; Minakawa, Noriaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c3cc44848g3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miyazawa, Tadashi</creatorcontrib><creatorcontrib>Umezaki, Kouhei</creatorcontrib><creatorcontrib>Tarashima, Noriko</creatorcontrib><creatorcontrib>Furukawa, Kazuhiro</creatorcontrib><creatorcontrib>Ooi, Takashi</creatorcontrib><creatorcontrib>Minakawa, Noriaki</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miyazawa, Tadashi</au><au>Umezaki, Kouhei</au><au>Tarashima, Noriko</au><au>Furukawa, Kazuhiro</au><au>Ooi, Takashi</au><au>Minakawa, Noriaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g</atitle><date>2013-08-08</date><risdate>2013</risdate><volume>49</volume><issue>71</issue><spage>7851</spage><epage>7853</epage><pages>7851-7853</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4′-thioribonucleoside and altritol nucleoside. The desired compound,
i.e.
, 1-[(3
R
,4
R
,5
S
,6
R
)-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil (
20
), was prepared
via
the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil.
The novel 1,2-dithianenucleoside was synthesized
via
Pummerer-like reaction followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.</abstract><doi>10.1039/c3cc44848g</doi><tpages>3</tpages></addata></record> |
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| title | Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g |
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