Loading…
Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate
Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.
Saved in:
| Published in: | Tetrahedron letters 2013-12, Vol.54 (50), p.6807-6809 |
|---|---|
| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113 |
| container_end_page | 6809 |
| container_issue | 50 |
| container_start_page | 6807 |
| container_title | Tetrahedron letters |
| container_volume | 54 |
| creator | Pan, Xianhua Li, Xiaojun Lu, Qingling Yu, Wansheng Li, Weijin Zhang, Qunhui Deng, Fei Liu, Feng |
| description | Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps. |
| doi_str_mv | 10.1016/j.tetlet.2013.09.136 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744709873</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403913017115</els_id><sourcerecordid>1744709873</sourcerecordid><originalsourceid>FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113</originalsourceid><addsrcrecordid>eNp9kEtPwzAQhC0EEuXxDzj4yIGENXad5IKEeEtI9ABcLeOuyZY0CbapVH49rsqZuexhZ0aaj7ETAaUAoc8XZcLUYSovQMgSmlJIvcMmoq5kIae12GUTAAWFAtnss4MYF5Cla5iwz1vvyRH2icd1n1qMFPngeaRkPzoaE_V8bIc4tjbhGbe8H1bY8ZvZrHh849S39E5pCGd8RTZ_XUvBdtz-UKA59ZgdCcMS55TjR2zP2y7i8d89ZK93ty_XD8XT8_3j9dVT4RRMU6Ea5ace55W03ivtag1eTlVVKbBZHlArVdXO5b-ua6mtrpSUDdQanRRCHrLTbe8Yhq9vjMksKTrsOtvj8B2NqHIemkwnW9XW6sIQY0BvxkBLG9ZGgNmwNQuzZWs2bA00JrPNscttDPOMFWEwccPQ5Z0BXTLzgf4v-AXjboVH</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744709873</pqid></control><display><type>article</type><title>Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate</title><source>ScienceDirect Freedom Collection 2022-2024</source><creator>Pan, Xianhua ; Li, Xiaojun ; Lu, Qingling ; Yu, Wansheng ; Li, Weijin ; Zhang, Qunhui ; Deng, Fei ; Liu, Feng</creator><creatorcontrib>Pan, Xianhua ; Li, Xiaojun ; Lu, Qingling ; Yu, Wansheng ; Li, Weijin ; Zhang, Qunhui ; Deng, Fei ; Liu, Feng</creatorcontrib><description>Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2013.09.136</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Aziridine ; Bromides ; Chemical reactions ; Derivatives ; Grignard reaction ; Inhibitors ; Phosphates ; Sitagliptin phosphate ; Synthesis ; Synthesis (chemistry) ; Tetrahedrons ; β-Amino acid</subject><ispartof>Tetrahedron letters, 2013-12, Vol.54 (50), p.6807-6809</ispartof><rights>2013 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113</citedby><cites>FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113</cites></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>Pan, Xianhua</creatorcontrib><creatorcontrib>Li, Xiaojun</creatorcontrib><creatorcontrib>Lu, Qingling</creatorcontrib><creatorcontrib>Yu, Wansheng</creatorcontrib><creatorcontrib>Li, Weijin</creatorcontrib><creatorcontrib>Zhang, Qunhui</creatorcontrib><creatorcontrib>Deng, Fei</creatorcontrib><creatorcontrib>Liu, Feng</creatorcontrib><title>Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate</title><title>Tetrahedron letters</title><description>Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.</description><subject>Aziridine</subject><subject>Bromides</subject><subject>Chemical reactions</subject><subject>Derivatives</subject><subject>Grignard reaction</subject><subject>Inhibitors</subject><subject>Phosphates</subject><subject>Sitagliptin phosphate</subject><subject>Synthesis</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>β-Amino acid</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kEtPwzAQhC0EEuXxDzj4yIGENXad5IKEeEtI9ABcLeOuyZY0CbapVH49rsqZuexhZ0aaj7ETAaUAoc8XZcLUYSovQMgSmlJIvcMmoq5kIae12GUTAAWFAtnss4MYF5Cla5iwz1vvyRH2icd1n1qMFPngeaRkPzoaE_V8bIc4tjbhGbe8H1bY8ZvZrHh849S39E5pCGd8RTZ_XUvBdtz-UKA59ZgdCcMS55TjR2zP2y7i8d89ZK93ty_XD8XT8_3j9dVT4RRMU6Ea5ace55W03ivtag1eTlVVKbBZHlArVdXO5b-ua6mtrpSUDdQanRRCHrLTbe8Yhq9vjMksKTrsOtvj8B2NqHIemkwnW9XW6sIQY0BvxkBLG9ZGgNmwNQuzZWs2bA00JrPNscttDPOMFWEwccPQ5Z0BXTLzgf4v-AXjboVH</recordid><startdate>20131211</startdate><enddate>20131211</enddate><creator>Pan, Xianhua</creator><creator>Li, Xiaojun</creator><creator>Lu, Qingling</creator><creator>Yu, Wansheng</creator><creator>Li, Weijin</creator><creator>Zhang, Qunhui</creator><creator>Deng, Fei</creator><creator>Liu, Feng</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20131211</creationdate><title>Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate</title><author>Pan, Xianhua ; Li, Xiaojun ; Lu, Qingling ; Yu, Wansheng ; Li, Weijin ; Zhang, Qunhui ; Deng, Fei ; Liu, Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aziridine</topic><topic>Bromides</topic><topic>Chemical reactions</topic><topic>Derivatives</topic><topic>Grignard reaction</topic><topic>Inhibitors</topic><topic>Phosphates</topic><topic>Sitagliptin phosphate</topic><topic>Synthesis</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>β-Amino acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pan, Xianhua</creatorcontrib><creatorcontrib>Li, Xiaojun</creatorcontrib><creatorcontrib>Lu, Qingling</creatorcontrib><creatorcontrib>Yu, Wansheng</creatorcontrib><creatorcontrib>Li, Weijin</creatorcontrib><creatorcontrib>Zhang, Qunhui</creatorcontrib><creatorcontrib>Deng, Fei</creatorcontrib><creatorcontrib>Liu, Feng</creatorcontrib><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><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pan, Xianhua</au><au>Li, Xiaojun</au><au>Lu, Qingling</au><au>Yu, Wansheng</au><au>Li, Weijin</au><au>Zhang, Qunhui</au><au>Deng, Fei</au><au>Liu, Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate</atitle><jtitle>Tetrahedron letters</jtitle><date>2013-12-11</date><risdate>2013</risdate><volume>54</volume><issue>50</issue><spage>6807</spage><epage>6809</epage><pages>6807-6809</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2013.09.136</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2013-12, Vol.54 (50), p.6807-6809 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744709873 |
| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | Aziridine Bromides Chemical reactions Derivatives Grignard reaction Inhibitors Phosphates Sitagliptin phosphate Synthesis Synthesis (chemistry) Tetrahedrons β-Amino acid |
| title | Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T11%3A12%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Efficient%20synthesis%20of%20sitagliptin%20phosphate,%20a%20novel%20DPP-IV%20inhibitor,%20via%20a%20chiral%20aziridine%20intermediate&rft.jtitle=Tetrahedron%20letters&rft.au=Pan,%20Xianhua&rft.date=2013-12-11&rft.volume=54&rft.issue=50&rft.spage=6807&rft.epage=6809&rft.pages=6807-6809&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/10.1016/j.tetlet.2013.09.136&rft_dat=%3Cproquest_cross%3E1744709873%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c405t-494f5fed73aff46c860f3547740aaaaf0e64478cc3af68836a674339086ec3113%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1744709873&rft_id=info:pmid/&rfr_iscdi=true |