A manufacturing process of 2',2'-difluoronucleoside and intermediate
The present invention relates to more improved process for preparing 2'-deoxy-2',2'-difluoronucleoside and its intermediate. The present invention provide a process for preparing an erythro enantiomer in greater than 98% purity, comprising forming a lactone ring by hydrolyzing ethyl (...
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creator | JUN-HO CHOI DAE-WON CHA MOON-SUNG KIM YONG-JIK KIM HONG-GYU LIM |
description | The present invention relates to more improved process for preparing 2'-deoxy-2',2'-difluoronucleoside and its intermediate. The present invention provide a process for preparing an erythro enantiomer in greater than 98% purity, comprising forming a lactone ring by hydrolyzing ethyl (3RS)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyloxolan-4-yl)propionate is hydrolyzed in the presence of hydrolysis reagents selected from acetic acid or chloroacetic acid, water and a mixture of organic solvents selected from the group comprising acetonilrile, dioxane, tetrahydrofuran or toluene, introducing a substituted benzoyl protecting group at the 3-position and 5-position, and recrys- tallizing said erythro enantiomer. Further, the present invention provides a process for selectively preparing, in greater than 99% purity, a beta-anomer 2'-deoxy-2',2'-difluoronucleoside at the 3'-position and 5'-position that are protected by a substituted benzoyl in a 2:3 alpha/beta anomeric ratio. |
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The present invention provide a process for preparing an erythro enantiomer in greater than 98% purity, comprising forming a lactone ring by hydrolyzing ethyl (3RS)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyloxolan-4-yl)propionate is hydrolyzed in the presence of hydrolysis reagents selected from acetic acid or chloroacetic acid, water and a mixture of organic solvents selected from the group comprising acetonilrile, dioxane, tetrahydrofuran or toluene, introducing a substituted benzoyl protecting group at the 3-position and 5-position, and recrys- tallizing said erythro enantiomer. Further, the present invention provides a process for selectively preparing, in greater than 99% purity, a beta-anomer 2'-deoxy-2',2'-difluoronucleoside at the 3'-position and 5'-position that are protected by a substituted benzoyl in a 2:3 alpha/beta anomeric ratio.</description><language>eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>2011</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20110203&DB=EPODOC&CC=AU&NR=2006325622B2$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25562,76317</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20110203&DB=EPODOC&CC=AU&NR=2006325622B2$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>JUN-HO CHOI</creatorcontrib><creatorcontrib>DAE-WON CHA</creatorcontrib><creatorcontrib>MOON-SUNG KIM</creatorcontrib><creatorcontrib>YONG-JIK KIM</creatorcontrib><creatorcontrib>HONG-GYU LIM</creatorcontrib><title>A manufacturing process of 2',2'-difluoronucleoside and intermediate</title><description>The present invention relates to more improved process for preparing 2'-deoxy-2',2'-difluoronucleoside and its intermediate. The present invention provide a process for preparing an erythro enantiomer in greater than 98% purity, comprising forming a lactone ring by hydrolyzing ethyl (3RS)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyloxolan-4-yl)propionate is hydrolyzed in the presence of hydrolysis reagents selected from acetic acid or chloroacetic acid, water and a mixture of organic solvents selected from the group comprising acetonilrile, dioxane, tetrahydrofuran or toluene, introducing a substituted benzoyl protecting group at the 3-position and 5-position, and recrys- tallizing said erythro enantiomer. Further, the present invention provides a process for selectively preparing, in greater than 99% purity, a beta-anomer 2'-deoxy-2',2'-difluoronucleoside at the 3'-position and 5'-position that are protected by a substituted benzoyl in a 2:3 alpha/beta anomeric ratio.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2011</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNyjsKwkAQANA0FqLeYQohjYEwwfSJHzyA1mHYnQ0Lm5llP_e38QBWr3n75j7BRlIdmVKTlxViUsM5gzrA9oJtZ70LVZNKNYE1e8tAYsFL4bSx9VT42Owchcynn4fm_Hy8b6-Ooy6cIxkWLsv0wb4fB7yOiPOMw5_tC42WM44</recordid><startdate>20110203</startdate><enddate>20110203</enddate><creator>JUN-HO CHOI</creator><creator>DAE-WON CHA</creator><creator>MOON-SUNG KIM</creator><creator>YONG-JIK KIM</creator><creator>HONG-GYU LIM</creator><scope>EVB</scope></search><sort><creationdate>20110203</creationdate><title>A manufacturing process of 2',2'-difluoronucleoside and intermediate</title><author>JUN-HO CHOI ; DAE-WON CHA ; MOON-SUNG KIM ; YONG-JIK KIM ; HONG-GYU LIM</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_AU2006325622BB23</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2011</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>JUN-HO CHOI</creatorcontrib><creatorcontrib>DAE-WON CHA</creatorcontrib><creatorcontrib>MOON-SUNG KIM</creatorcontrib><creatorcontrib>YONG-JIK KIM</creatorcontrib><creatorcontrib>HONG-GYU LIM</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>JUN-HO CHOI</au><au>DAE-WON CHA</au><au>MOON-SUNG KIM</au><au>YONG-JIK KIM</au><au>HONG-GYU LIM</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>A manufacturing process of 2',2'-difluoronucleoside and intermediate</title><date>2011-02-03</date><risdate>2011</risdate><abstract>The present invention relates to more improved process for preparing 2'-deoxy-2',2'-difluoronucleoside and its intermediate. The present invention provide a process for preparing an erythro enantiomer in greater than 98% purity, comprising forming a lactone ring by hydrolyzing ethyl (3RS)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyloxolan-4-yl)propionate is hydrolyzed in the presence of hydrolysis reagents selected from acetic acid or chloroacetic acid, water and a mixture of organic solvents selected from the group comprising acetonilrile, dioxane, tetrahydrofuran or toluene, introducing a substituted benzoyl protecting group at the 3-position and 5-position, and recrys- tallizing said erythro enantiomer. Further, the present invention provides a process for selectively preparing, in greater than 99% purity, a beta-anomer 2'-deoxy-2',2'-difluoronucleoside at the 3'-position and 5'-position that are protected by a substituted benzoyl in a 2:3 alpha/beta anomeric ratio.</abstract><oa>free_for_read</oa></addata></record> |
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subjects | CHEMISTRY HETEROCYCLIC COMPOUNDS METALLURGY ORGANIC CHEMISTRY |
title | A manufacturing process of 2',2'-difluoronucleoside and intermediate |
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