{"id":"https://openalex.org/W2007014516","doi":"https://doi.org/10.1021/jo902616s","title":"Preparation of the 2\u2032-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation","display_name":"Preparation of the 2\u2032-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation","publication_year":2010,"publication_date":"2010-02-10","ids":{"openalex":"https://openalex.org/W2007014516","doi":"https://doi.org/10.1021/jo902616s","mag":"2007014516","pmid":"https://pubmed.ncbi.nlm.nih.gov/20146451"},"language":"en","primary_location":{"id":"doi:10.1021/jo902616s","doi":"https://doi.org/10.1021/jo902616s","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo902616s","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"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/A5012789277","display_name":"Joseph W. Arico","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I103531236","display_name":"Boston College","ror":"https://ror.org/02n2fzt79","country_code":"US","type":"education","lineage":["https://openalex.org/I103531236"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Joseph W. Arico","raw_affiliation_strings":["Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467","Department of Chemistry , Merkert Chemistry Center , Boston College , Chestnut Hill , Massachusetts 02467 , USA "],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467","institution_ids":["https://openalex.org/I103531236"]},{"raw_affiliation_string":"Department of Chemistry , Merkert Chemistry Center , Boston College , Chestnut Hill , Massachusetts 02467 , USA ","institution_ids":["https://openalex.org/I103531236"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5048361489","display_name":"Amy K. Calhoun","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I103531236","display_name":"Boston College","ror":"https://ror.org/02n2fzt79","country_code":"US","type":"education","lineage":["https://openalex.org/I103531236"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Amy K. Calhoun","raw_affiliation_strings":["Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467","institution_ids":["https://openalex.org/I103531236"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5033260170","display_name":"Larry W. McLaughlin","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I103531236","display_name":"Boston College","ror":"https://ror.org/02n2fzt79","country_code":"US","type":"education","lineage":["https://openalex.org/I103531236"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Larry W. McLaughlin","raw_affiliation_strings":["Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467","institution_ids":["https://openalex.org/I103531236"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I103531236"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.4164,"has_fulltext":false,"cited_by_count":12,"citation_normalized_percentile":{"value":0.534414,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":97},"biblio":{"volume":"75","issue":"5","first_page":"1360","last_page":"1365"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10432","display_name":"DNA and Nucleic Acid Chemistry","score":0.8935999870300293,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10432","display_name":"DNA and Nucleic Acid Chemistry","score":0.8935999870300293,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.07479999959468842,"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/T12827","display_name":"Biochemical and Molecular Research","score":0.005499999970197678,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/2-deoxynucleosides","display_name":"2'-deoxyribonucleosides","score":0.875},{"id":"https://openalex.org/keywords/2-6-diaminopurine","display_name":"2,6-diaminopurine","score":0.9959999918937683},{"id":"https://openalex.org/keywords/isoguanine","display_name":"isoguanine","score":0.9769999980926514},{"id":"https://openalex.org/keywords/diazotization","display_name":"diazotization","score":0.8100000023841858},{"id":"https://openalex.org/keywords/silylation","display_name":"silylation","score":0.6639999747276306},{"id":"https://openalex.org/keywords/nucleoside-synthesis","display_name":"nucleoside synthesis","score":0.6869999766349792}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9488780498504639},{"id":"https://openalex.org/C2777313579","wikidata":"https://www.wikidata.org/wiki/Q898365","display_name":"Glycosylation","level":2,"score":0.7406230568885803},{"id":"https://openalex.org/C2776476023","wikidata":"https://www.wikidata.org/wiki/Q188261","display_name":"Purine","level":3,"score":0.660109281539917},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.6144111752510071},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.5725568532943726},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.5009229183197021},{"id":"https://openalex.org/C2776543447","wikidata":"https://www.wikidata.org/wiki/Q28734","display_name":"Nucleoside","level":2,"score":0.47828230261802673},{"id":"https://openalex.org/C2776371256","wikidata":"https://www.wikidata.org/wiki/Q12370","display_name":"Salt (chemistry)","level":2,"score":0.4209059476852417},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3878345489501953},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.36123448610305786},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3186265528202057},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.13837873935699463},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.07724323868751526},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C106159729","wikidata":"https://www.wikidata.org/wiki/Q2294553","display_name":"Financial economics","level":1,"score":0.0},{"id":"https://openalex.org/C162324750","wikidata":"https://www.wikidata.org/wiki/Q8134","display_name":"Economics","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}],"mesh":[{"descriptor_ui":"D000241","descriptor_name":"Adenosine","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006031","descriptor_name":"Glycosylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006147","descriptor_name":"Guanine","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D006147","descriptor_name":"Guanine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D006151","descriptor_name":"Guanosine","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D006151","descriptor_name":"Guanosine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011684","descriptor_name":"Purine Nucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011684","descriptor_name":"Purine Nucleosides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015075","descriptor_name":"2-Aminopurine","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D015075","descriptor_name":"2-Aminopurine","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D015075","descriptor_name":"2-Aminopurine","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo902616s","doi":"https://doi.org/10.1021/jo902616s","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo902616s","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:20146451","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/20146451","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":24,"referenced_works":["https://openalex.org/W1524705448","https://openalex.org/W1528957630","https://openalex.org/W1593933438","https://openalex.org/W1972559540","https://openalex.org/W1973348322","https://openalex.org/W1975194563","https://openalex.org/W1975309023","https://openalex.org/W1979028182","https://openalex.org/W1990734020","https://openalex.org/W2000145226","https://openalex.org/W2033912644","https://openalex.org/W2035210877","https://openalex.org/W2035706554","https://openalex.org/W2049953363","https://openalex.org/W2056414768","https://openalex.org/W2064648843","https://openalex.org/W2065164352","https://openalex.org/W2084217994","https://openalex.org/W2088430073","https://openalex.org/W2124665870","https://openalex.org/W2161762313","https://openalex.org/W2173533189","https://openalex.org/W2319608388","https://openalex.org/W2951708605"],"related_works":["https://openalex.org/W2046723551","https://openalex.org/W4378710458","https://openalex.org/W2950774654","https://openalex.org/W1997775119","https://openalex.org/W2023064203","https://openalex.org/W1984292420","https://openalex.org/W2008025943","https://openalex.org/W7097293909","https://openalex.org/W2124665870","https://openalex.org/W2952578461"],"abstract_inverted_index":{"The":[0,38,75,89],"purine":[1,17,39],"nucleoside":[2],"2,6-diaminopurine-2'-deoxyriboside":[3],"is":[4,30,42,69,77,87,92],"prepared":[5,31,43],"by":[6,34,44],"the":[7,11,15,25,53,62,66,72,80,84],"direct":[8],"glycosylation":[9],"of":[10,14,47,61],"2,6-bis(tetramethylsuccinimide)":[12],"derivative":[13,55],"parent":[16],"heterocycle":[18,40],"4":[19],"with":[20,64],"2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl":[21],"chloride":[22],"5":[23],"using":[24],"sodium":[26],"salt":[27],"method.":[28],"2'-Deoxyisoguanosine":[29],"from":[32],"2,6-diaminopurine":[33,48],"a":[35],"five-step":[36],"procedure.":[37],"isoguanine":[41],"selective":[45],"diazotization":[46],"and":[49,83],"then":[50],"converted":[51],"to":[52,56,97],"N9-trityl":[54],"increase":[57],"solubility.":[58],"After":[59],"silylation":[60],"O(2)-carbonyl":[63,76],"TMSCl,":[65],"N(6)-amino":[67],"group":[68,86],"protected":[70,78,100],"as":[71,79],"tetramethylsuccinimide":[73],"(M(4)SI).":[74],"DPC":[81],"derivative,":[82],"trityl":[85],"removed.":[88],"resulting":[90],"product":[91],"glycosylated":[93],"in":[94],"good":[95],"yield":[96],"generate":[98],"fully":[99],"2'-deoxyisoguanosine.":[101]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2012,"cited_by_count":4}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
