PubMed:2620298 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/2620298","sourcedb":"PubMed","sourceid":"2620298","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/2620298","text":"Stereoselective synthesis of 1,1-dialkyl-1-methoxymethyl glucosides (acetal-glucosides).\nThe synthesis is described of highly acid-sensitive, 1,1-dialkyl-1-methoxymethyl glucosides (acetal-glucosides) as potential anti-cancer prodrugs. Reaction of 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-beta-D-glucopyranose (4) severally with various aliphatic and alicyclic ketones and methyl trimethylsilyl ether, in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate, afforded the corresponding acetylated acetal-beta-glucosides, e.g., acetone gave 1-methoxy-1-methylethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (7a). Likewise the alpha-anomer (8a) of 7a was obtained from the alpha-anomer of 4. Deacetylation of the tetra-acetates then gave the acetal-alpha- and -beta-glucosides.","tracks":[{"project":"PubmedHPO","denotations":[{"id":"T1","span":{"begin":219,"end":225},"obj":"HP_0002664"}],"attributes":[{"subj":"T1","pred":"source","obj":"PubmedHPO"}]},{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":88},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":89,"end":235},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":236,"end":641},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":642,"end":719},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":720,"end":805},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":88},"obj":"Sentence"},{"id":"T2","span":{"begin":89,"end":235},"obj":"Sentence"},{"id":"T3","span":{"begin":236,"end":641},"obj":"Sentence"},{"id":"T4","span":{"begin":642,"end":719},"obj":"Sentence"},{"id":"T5","span":{"begin":720,"end":805},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"attributes":[{"subj":"TextSentencer_T1","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T2","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T3","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T4","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T5","pred":"source","obj":"sentences"},{"subj":"T1","pred":"source","obj":"sentences"},{"subj":"T2","pred":"source","obj":"sentences"},{"subj":"T3","pred":"source","obj":"sentences"},{"subj":"T4","pred":"source","obj":"sentences"},{"subj":"T5","pred":"source","obj":"sentences"}]},{"project":"NCBITAXON","denotations":[{"id":"T1","span":{"begin":256,"end":263},"obj":"OrganismTaxon"},{"id":"T2","span":{"begin":598,"end":605},"obj":"OrganismTaxon"}],"attributes":[{"id":"A1","pred":"db_id","subj":"T1","obj":"100829"},{"id":"A2","pred":"db_id","subj":"T2","obj":"100829"},{"subj":"T1","pred":"source","obj":"NCBITAXON"},{"subj":"T2","pred":"source","obj":"NCBITAXON"}]},{"project":"mondo_disease","denotations":[{"id":"T1","span":{"begin":219,"end":225},"obj":"Disease"}],"attributes":[{"id":"A1","pred":"mondo_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/MONDO_0004992"},{"subj":"T1","pred":"source","obj":"mondo_disease"}]},{"project":"HP-phenotype","denotations":[{"id":"T1","span":{"begin":219,"end":225},"obj":"Phenotype"}],"attributes":[{"id":"A1","pred":"hp_id","subj":"T1","obj":"HP:0002664"},{"subj":"T1","pred":"source","obj":"HP-phenotype"}],"namespaces":[{"prefix":"HP","uri":"http://purl.obolibrary.org/obo/HP_"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"PubmedHPO","color":"#b693ec","default":true},{"id":"sentences","color":"#93ec9c"},{"id":"NCBITAXON","color":"#ec93a3"},{"id":"mondo_disease","color":"#93bdec"},{"id":"HP-phenotype","color":"#d7ec93"}]}]}}