Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions
The titanium-mediated cyclopropanation reaction using Ti(O i Pr) 3Me/EtMgBr/BF 3·OEt 2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron 2012-02, Vol.68 (6), p.1802-1809 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1809 |
|---|---|
| container_issue | 6 |
| container_start_page | 1802 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Declerck, Delphine Nguyen Van Nhien, Albert Josse, Solen Szymoniak, Jan Bertus, Philippe Bello, Claudia Vogel, Pierre Postel, Denis |
| description | The titanium-mediated cyclopropanation reaction using Ti(O
i
Pr)
3Me/EtMgBr/BF
3·OEt
2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the
trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2
S,3
S,4
R,5
S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (
38), which has the same absolute configuration as
l-fucose, is a moderate (
IC
50=44 μM), but selective, inhibitor of α-
l-fucosidase from human placenta.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.12.024 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00711775v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402011019077</els_id><sourcerecordid>1744686661</sourcerecordid><originalsourceid>FETCH-LOGICAL-c394t-5074d31994a4a14a54b5444fdec3ef6ec535a17cdcae77f0c509f28c7213afd83</originalsourceid><addsrcrecordid>eNp9kUGLFDEQhRtRcFz9Ad76IuyCaZN0OpnB07KsrjDgQT2HMql2a8gkbZIZ6H9vN7Ps0VMVxVevqPea5r3gneBCfzp0FWsnuRCdkB2X6kWzEUorNiihXzYbzhVnikv-unlTyoHzhZT9psk_5lgfsVBp09hKdi0YHCkmN7uQppymOdxMc84pkKeIrP-omKcUWo-ZzlDpjKWFaQozxT9tpQqRTkd2RE9Q0bcZwVVKsXUpelq78rZ5NUIo-O6pXjW_vtz_vHtg--9fv93d7pnrd6qygRvle7HbKVAgFAzq96CUGj26HkeNbugHEMZ5B2jMyN3Ad6PcOiNFD6Pf9lfNzUX3EYKdMh0hzzYB2YfbvV1nnBshjBnOYmGvL-zy8t8TlmqPVByGABHTqVhhlNJbrfWKigvqciol4_isLbhds7AHu2Rh1yyskHbJYtn58CQPxUEYM0RH5XlRDloro8zCfb5wuPhyJsy2OMLoFjczump9ov9c-Qe2L5_V</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744686661</pqid></control><display><type>article</type><title>Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions</title><source>Elsevier ScienceDirect Journals</source><creator>Declerck, Delphine ; Nguyen Van Nhien, Albert ; Josse, Solen ; Szymoniak, Jan ; Bertus, Philippe ; Bello, Claudia ; Vogel, Pierre ; Postel, Denis</creator><creatorcontrib>Declerck, Delphine ; Nguyen Van Nhien, Albert ; Josse, Solen ; Szymoniak, Jan ; Bertus, Philippe ; Bello, Claudia ; Vogel, Pierre ; Postel, Denis</creatorcontrib><description>The titanium-mediated cyclopropanation reaction using Ti(O
i
Pr)
3Me/EtMgBr/BF
3·OEt
2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the
trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2
S,3
S,4
R,5
S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (
38), which has the same absolute configuration as
l-fucose, is a moderate (
IC
50=44 μM), but selective, inhibitor of α-
l-fucosidase from human placenta.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.12.024</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>2-Cyanopyrrolidine ; Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemical Sciences ; Chemistry ; Cyclopropylamine ; Derivatives ; Dideoxyiminoalditols ; Exact sciences and technology ; Glycosidases ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Human ; Inhibitors ; Kulinkovich reaction ; Organic chemistry ; Placenta ; Polyols ; Preparations and properties ; Synthesis (chemistry) ; Tetrahedrons ; Titanium ; α- l-Fucosidase inhibition</subject><ispartof>Tetrahedron, 2012-02, Vol.68 (6), p.1802-1809</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c394t-5074d31994a4a14a54b5444fdec3ef6ec535a17cdcae77f0c509f28c7213afd83</citedby><cites>FETCH-LOGICAL-c394t-5074d31994a4a14a54b5444fdec3ef6ec535a17cdcae77f0c509f28c7213afd83</cites><orcidid>0000-0002-1174-5097 ; 0000-0002-1956-1153 ; 0000-0002-1346-2576</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402011019077$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25664747$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00711775$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Declerck, Delphine</creatorcontrib><creatorcontrib>Nguyen Van Nhien, Albert</creatorcontrib><creatorcontrib>Josse, Solen</creatorcontrib><creatorcontrib>Szymoniak, Jan</creatorcontrib><creatorcontrib>Bertus, Philippe</creatorcontrib><creatorcontrib>Bello, Claudia</creatorcontrib><creatorcontrib>Vogel, Pierre</creatorcontrib><creatorcontrib>Postel, Denis</creatorcontrib><title>Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions</title><title>Tetrahedron</title><description>The titanium-mediated cyclopropanation reaction using Ti(O
i
Pr)
3Me/EtMgBr/BF
3·OEt
2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the
trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2
S,3
S,4
R,5
S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (
38), which has the same absolute configuration as
l-fucose, is a moderate (
IC
50=44 μM), but selective, inhibitor of α-
l-fucosidase from human placenta.
[Display omitted]</description><subject>2-Cyanopyrrolidine</subject><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Cyclopropylamine</subject><subject>Derivatives</subject><subject>Dideoxyiminoalditols</subject><subject>Exact sciences and technology</subject><subject>Glycosidases</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Human</subject><subject>Inhibitors</subject><subject>Kulinkovich reaction</subject><subject>Organic chemistry</subject><subject>Placenta</subject><subject>Polyols</subject><subject>Preparations and properties</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Titanium</subject><subject>α- l-Fucosidase inhibition</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kUGLFDEQhRtRcFz9Ad76IuyCaZN0OpnB07KsrjDgQT2HMql2a8gkbZIZ6H9vN7Ps0VMVxVevqPea5r3gneBCfzp0FWsnuRCdkB2X6kWzEUorNiihXzYbzhVnikv-unlTyoHzhZT9psk_5lgfsVBp09hKdi0YHCkmN7uQppymOdxMc84pkKeIrP-omKcUWo-ZzlDpjKWFaQozxT9tpQqRTkd2RE9Q0bcZwVVKsXUpelq78rZ5NUIo-O6pXjW_vtz_vHtg--9fv93d7pnrd6qygRvle7HbKVAgFAzq96CUGj26HkeNbugHEMZ5B2jMyN3Ad6PcOiNFD6Pf9lfNzUX3EYKdMh0hzzYB2YfbvV1nnBshjBnOYmGvL-zy8t8TlmqPVByGABHTqVhhlNJbrfWKigvqciol4_isLbhds7AHu2Rh1yyskHbJYtn58CQPxUEYM0RH5XlRDloro8zCfb5wuPhyJsy2OMLoFjczump9ov9c-Qe2L5_V</recordid><startdate>20120211</startdate><enddate>20120211</enddate><creator>Declerck, Delphine</creator><creator>Nguyen Van Nhien, Albert</creator><creator>Josse, Solen</creator><creator>Szymoniak, Jan</creator><creator>Bertus, Philippe</creator><creator>Bello, Claudia</creator><creator>Vogel, Pierre</creator><creator>Postel, Denis</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-1174-5097</orcidid><orcidid>https://orcid.org/0000-0002-1956-1153</orcidid><orcidid>https://orcid.org/0000-0002-1346-2576</orcidid></search><sort><creationdate>20120211</creationdate><title>Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions</title><author>Declerck, Delphine ; Nguyen Van Nhien, Albert ; Josse, Solen ; Szymoniak, Jan ; Bertus, Philippe ; Bello, Claudia ; Vogel, Pierre ; Postel, Denis</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c394t-5074d31994a4a14a54b5444fdec3ef6ec535a17cdcae77f0c509f28c7213afd83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>2-Cyanopyrrolidine</topic><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Cyclopropylamine</topic><topic>Derivatives</topic><topic>Dideoxyiminoalditols</topic><topic>Exact sciences and technology</topic><topic>Glycosidases</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Human</topic><topic>Inhibitors</topic><topic>Kulinkovich reaction</topic><topic>Organic chemistry</topic><topic>Placenta</topic><topic>Polyols</topic><topic>Preparations and properties</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Titanium</topic><topic>α- l-Fucosidase inhibition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Declerck, Delphine</creatorcontrib><creatorcontrib>Nguyen Van Nhien, Albert</creatorcontrib><creatorcontrib>Josse, Solen</creatorcontrib><creatorcontrib>Szymoniak, Jan</creatorcontrib><creatorcontrib>Bertus, Philippe</creatorcontrib><creatorcontrib>Bello, Claudia</creatorcontrib><creatorcontrib>Vogel, Pierre</creatorcontrib><creatorcontrib>Postel, Denis</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Declerck, Delphine</au><au>Nguyen Van Nhien, Albert</au><au>Josse, Solen</au><au>Szymoniak, Jan</au><au>Bertus, Philippe</au><au>Bello, Claudia</au><au>Vogel, Pierre</au><au>Postel, Denis</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions</atitle><jtitle>Tetrahedron</jtitle><date>2012-02-11</date><risdate>2012</risdate><volume>68</volume><issue>6</issue><spage>1802</spage><epage>1809</epage><pages>1802-1809</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>The titanium-mediated cyclopropanation reaction using Ti(O
i
Pr)
3Me/EtMgBr/BF
3·OEt
2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the
trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2
S,3
S,4
R,5
S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (
38), which has the same absolute configuration as
l-fucose, is a moderate (
IC
50=44 μM), but selective, inhibitor of α-
l-fucosidase from human placenta.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2011.12.024</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-1174-5097</orcidid><orcidid>https://orcid.org/0000-0002-1956-1153</orcidid><orcidid>https://orcid.org/0000-0002-1346-2576</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-02, Vol.68 (6), p.1802-1809 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00711775v1 |
| source | Elsevier ScienceDirect Journals |
| subjects | 2-Cyanopyrrolidine Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemical Sciences Chemistry Cyclopropylamine Derivatives Dideoxyiminoalditols Exact sciences and technology Glycosidases Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Human Inhibitors Kulinkovich reaction Organic chemistry Placenta Polyols Preparations and properties Synthesis (chemistry) Tetrahedrons Titanium α- l-Fucosidase inhibition |
| title | Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T10%3A04%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%202-(1-aminocyclopropyl)pyrrolidine-3,4-diol%20derivatives%20applying%20titanium-mediated%20reaction%20conditions&rft.jtitle=Tetrahedron&rft.au=Declerck,%20Delphine&rft.date=2012-02-11&rft.volume=68&rft.issue=6&rft.spage=1802&rft.epage=1809&rft.pages=1802-1809&rft.issn=0040-4020&rft.eissn=1464-5416&rft.coden=TETRAB&rft_id=info:doi/10.1016/j.tet.2011.12.024&rft_dat=%3Cproquest_hal_p%3E1744686661%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1744686661&rft_id=info:pmid/&rft_els_id=S0040402011019077&rfr_iscdi=true |