Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol
This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-gro...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2020/10/01, Vol.68(10), pp.996-1000 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 68 |
| creator | Sakata, Juri Akita, Kazunari Sato, Manabu Shimomura, Masashi Tokuyama, Hidetoshi |
| description | This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry. |
| doi_str_mv | 10.1248/cpb.c20-00531 |
| format | Article |
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An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c20-00531</identifier><identifier>PMID: 32999152</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Alcohols ; amino alcohol ; Amino Alcohols - chemistry ; Coordination Complexes - chemistry ; cyclic sulfamidite ; deprotection ; Heterocyclic Compounds - chemical synthesis ; Imidazoles - chemistry ; Oxidation-Reduction ; Phenols - chemistry ; protecting group ; protection ; Pyridines - chemistry ; Ruthenium - chemistry ; Stereochemistry ; Substrates ; Sulfhydryl Compounds - chemistry ; Thiophenol</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2020/10/01, Vol.68(10), pp.996-1000</ispartof><rights>2020 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c635t-5c102937ed0d4a4f4d8404bc00691896a78321f3dc92199f3f9a358eaefcabd13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32999152$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sakata, Juri</creatorcontrib><creatorcontrib>Akita, Kazunari</creatorcontrib><creatorcontrib>Sato, Manabu</creatorcontrib><creatorcontrib>Shimomura, Masashi</creatorcontrib><creatorcontrib>Tokuyama, Hidetoshi</creatorcontrib><creatorcontrib>Graduate School of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Tohoku University</creatorcontrib><title>Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.</description><subject>Alcohols</subject><subject>amino alcohol</subject><subject>Amino Alcohols - chemistry</subject><subject>Coordination Complexes - chemistry</subject><subject>cyclic sulfamidite</subject><subject>deprotection</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Imidazoles - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Phenols - chemistry</subject><subject>protecting group</subject><subject>protection</subject><subject>Pyridines - chemistry</subject><subject>Ruthenium - chemistry</subject><subject>Stereochemistry</subject><subject>Substrates</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Thiophenol</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc9vFCEYhonR2LV69GpIvHiZ-gHzC2-bra4mNZq0PROWgS4bBkaYMendP1x2Zt0mXoZkeHi-F16E3hK4IrRsP6phd6UoFAAVI8_QirCyKSpK2XO0AgBeUFazC_QqpQMAraBhL9EFo5xzUtEV-rN5VM4qfDs5I3vb2VFjmfCt7Sc3Sq_DlPDPGEatRusf8DaGacAmRLzurQ947VTYB5c-4Wv9W7sw9NqPOBgs8Xfruvx3OB0OfvYEFRy-T0fX3d6GYa99cK_RCyNd0m9O6yW6__L5bvO1uPmx_bZZ3xSqZtVYVIoA5azRHXSlLE3ZtSWUOwVQc9LyWjYto8SwTnFKODfMcMmqVkttlNx1hF2iD4s3h_o16TSK3ialnVsuKmhZZkXLKcvo-__QQ5iiz-lmijctBchUsVAqhpSiNmKItpfxURAQx3pErkfkesRcT-bfnazTrtfdmf7XRwa2C5B3rZIueGe9fpqtUqP2ureCwiytW3JcWgGc13lozlRTlt8om64X0yGN8kGfR8k4WuX0HKxujznz95zwaXsvo9Ce_QXNs7rE</recordid><startdate>20201001</startdate><enddate>20201001</enddate><creator>Sakata, Juri</creator><creator>Akita, Kazunari</creator><creator>Sato, Manabu</creator><creator>Shimomura, Masashi</creator><creator>Tokuyama, Hidetoshi</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20201001</creationdate><title>Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol</title><author>Sakata, Juri ; Akita, Kazunari ; Sato, Manabu ; Shimomura, Masashi ; Tokuyama, Hidetoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c635t-5c102937ed0d4a4f4d8404bc00691896a78321f3dc92199f3f9a358eaefcabd13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohols</topic><topic>amino alcohol</topic><topic>Amino Alcohols - chemistry</topic><topic>Coordination Complexes - chemistry</topic><topic>cyclic sulfamidite</topic><topic>deprotection</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Imidazoles - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Phenols - chemistry</topic><topic>protecting group</topic><topic>protection</topic><topic>Pyridines - chemistry</topic><topic>Ruthenium - chemistry</topic><topic>Stereochemistry</topic><topic>Substrates</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Thiophenol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sakata, Juri</creatorcontrib><creatorcontrib>Akita, Kazunari</creatorcontrib><creatorcontrib>Sato, Manabu</creatorcontrib><creatorcontrib>Shimomura, Masashi</creatorcontrib><creatorcontrib>Tokuyama, Hidetoshi</creatorcontrib><creatorcontrib>Graduate School of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Tohoku University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sakata, Juri</au><au>Akita, Kazunari</au><au>Sato, Manabu</au><au>Shimomura, Masashi</au><au>Tokuyama, Hidetoshi</au><aucorp>Graduate School of Pharmaceutical Sciences</aucorp><aucorp>Tohoku University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2020-10-01</date><risdate>2020</risdate><volume>68</volume><issue>10</issue><spage>996</spage><epage>1000</epage><pages>996-1000</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>32999152</pmid><doi>10.1248/cpb.c20-00531</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | Alcohols amino alcohol Amino Alcohols - chemistry Coordination Complexes - chemistry cyclic sulfamidite deprotection Heterocyclic Compounds - chemical synthesis Imidazoles - chemistry Oxidation-Reduction Phenols - chemistry protecting group protection Pyridines - chemistry Ruthenium - chemistry Stereochemistry Substrates Sulfhydryl Compounds - chemistry Thiophenol |
| title | Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol |
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