{"id":"https://openalex.org/W2072008474","doi":"https://doi.org/10.1039/p19890001619","title":"Stereoselective synthesis of 5,5-dimethyl-2-oxo-2-(3,4,6-tri-O-acetyl-2-deoxy-\u03b1- D -hexopyranosylseleno)-1,3,2-dioxaphosphorinane: novel observations on the selenono\u2013selenolo isomerization of phosphoroselenoates","display_name":"Stereoselective synthesis of 5,5-dimethyl-2-oxo-2-(3,4,6-tri-O-acetyl-2-deoxy-\u03b1- D -hexopyranosylseleno)-1,3,2-dioxaphosphorinane: novel observations on the selenono\u2013selenolo isomerization of phosphoroselenoates","publication_year":1989,"publication_date":"1989-01-01","ids":{"openalex":"https://openalex.org/W2072008474","doi":"https://doi.org/10.1039/p19890001619","mag":"2072008474"},"language":"en","primary_location":{"id":"doi:10.1039/p19890001619","doi":"https://doi.org/10.1039/p19890001619","is_oa":false,"landing_page_url":"https://doi.org/10.1039/p19890001619","pdf_url":null,"source":{"id":"https://openalex.org/S955628534","display_name":"Journal of the Chemical Society Perkin Transactions 1","issn_l":"1364-5463","issn":["1364-5463","1470-4358","1472-7781","2050-8263"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"J. Chem. Soc., Perkin Trans. 1","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5009190356","display_name":"Maria Michalska","orcid":"https://orcid.org/0000-0003-4344-3832","observed_orcids":["https://orcid.org/0000-0003-4344-3832"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Maria Michalska","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5061775447","display_name":"Joanna Borowiecka","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Joanna Borowiecka","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5067438303","display_name":"Pawe\u0142 Lipka","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Pawe\u0142 Lipka","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5076360745","display_name":"T. ROKITA\u2010TRYGUBOWICZ","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Teresa Rokita-Trygubowicz","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.4777,"has_fulltext":false,"cited_by_count":10,"citation_normalized_percentile":{"value":0.53618628,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":93},"biblio":{"volume":null,"issue":"9","first_page":"1619","last_page":"1622"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11931","display_name":"Organoselenium and organotellurium chemistry","score":0.5630000233650208,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11931","display_name":"Organoselenium and organotellurium chemistry","score":0.5630000233650208,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.3815999925136566,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T11748","display_name":"Organophosphorus compounds synthesis","score":0.041600000113248825,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/2-deoxy-sugars","display_name":"2-deoxy sugars","score":0.875},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.8100000023841858},{"id":"https://openalex.org/keywords/selenophosphate","display_name":"selenophosphate","score":0.46399998664855957}],"concepts":[{"id":"https://openalex.org/C126661725","wikidata":"https://www.wikidata.org/wiki/Q903420","display_name":"Isomerization","level":3,"score":0.9176152348518372},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.872662365436554},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.8039073944091797},{"id":"https://openalex.org/C2776300020","wikidata":"https://www.wikidata.org/wiki/Q422423","display_name":"Bromide","level":2,"score":0.6513646245002747},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.5836291313171387},{"id":"https://openalex.org/C200093464","wikidata":"https://www.wikidata.org/wiki/Q166583","display_name":"Condensation","level":2,"score":0.5189380645751953},{"id":"https://openalex.org/C171560689","wikidata":"https://www.wikidata.org/wiki/Q193086","display_name":"Halide","level":2,"score":0.48963814973831177},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.40428510308265686},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3765978515148163},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.3528820276260376},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.23226457834243774},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0},{"id":"https://openalex.org/C97355855","wikidata":"https://www.wikidata.org/wiki/Q11473","display_name":"Thermodynamics","level":1,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1039/p19890001619","doi":"https://doi.org/10.1039/p19890001619","is_oa":false,"landing_page_url":"https://doi.org/10.1039/p19890001619","pdf_url":null,"source":{"id":"https://openalex.org/S955628534","display_name":"Journal of the Chemical Society Perkin Transactions 1","issn_l":"1364-5463","issn":["1364-5463","1470-4358","1472-7781","2050-8263"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"J. Chem. Soc., Perkin Trans. 1","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2950914943","https://openalex.org/W2008776185","https://openalex.org/W2398531383","https://openalex.org/W2030283286","https://openalex.org/W2321827098","https://openalex.org/W2951671072","https://openalex.org/W2462603149","https://openalex.org/W2011641290","https://openalex.org/W2105463506","https://openalex.org/W2949618047"],"abstract_inverted_index":{"The":[0],"first":[1],"example":[2],"of":[3,6,19,31,41,62],"a":[4,7],"1-phosphoroselenoate":[5],"2-deoxy":[8],"sugar":[9],"has":[10,66],"been":[11,67],"obtained":[12],"by":[13,26,92,102],"three":[14],"independent":[15],"routes:":[16],"(A)":[17,78],"selenophosphorylation":[18],"3,4,6-tri-O-acetyl-2-deoxy-D-arabino-hexopyranose":[20],"(4)":[21],"with":[22,35,52],"selenophosphorochloridate":[23],"(5)":[24],"followed":[25],"selenono\u2013selenolo":[27,71,98],"isomerization;":[28],"(B)":[29],"condensation":[30],"3,4,6-tri-O-acetyl-2-deoxy-\u03b1-D-arabino-hexopyranosyl":[32],"bromide":[33],"(8)":[34],"O,O-dialkylphosphoroselenoate":[36],"(9),":[37],"and":[38,55],"(C)":[39],"addition":[40],"O,O-dialkylphosphoroselenoic":[42],"acid":[43],"(11)":[44],"to":[45,58],"3,4,6-tri-O-acetyl-D-glucal":[46],"(1).":[47],"All":[48],"these":[49],"reactions":[50],"proceed":[51],"high":[53],"yield":[54],"full":[56],"stereoselectivity":[57],"afford":[59],"the":[60,70,81,89,97],"\u03b1-selenophosphate":[61],"2-deoxy-D-arabino-hexopyranose":[63],"(7).":[64],"It":[65],"shown":[68],"that":[69],"isomerization":[72],"(6)\u2192(7)":[73],"which":[74],"occurs":[75],"in":[76],"route":[77],"proceeds":[79],"via":[80],"intermediate":[82],"2-deoxyglycosyl":[83],"chloride":[84],"(12).":[85],"This":[86],"finding":[87],"confirms":[88],"mechanism":[90],"proposed":[91],"Chabrier":[93],"et":[94],"al.":[95],"for":[96],"phosphate":[99],"Isomerization":[100],"catalyzed":[101],"ammonium":[103],"halides.":[104]},"counts_by_year":[{"year":2024,"cited_by_count":1}],"updated_date":"2026-08-21T09:56:20.448147","created_date":"2016-06-24T00:00:00"}
