PubMed:1797378 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/1797378","sourcedb":"PubMed","sourceid":"1797378","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/1797378","text":"Synthesis of 1-(3-azido-2,3-dideoxy-beta-D-allofuranosyl)thymine, 1-(2,3-dideoxy-beta-D-allofuranosyl)thymine, and 1-(2,3-dideoxy-beta-D-erythro-hex-2-enofuranosyl)thymine.\n1-(2-O-Acetyl-3,5,6-tri-O-benzoyl-beta-D-glucofuranosyl)thymine (1) was converted into the 2,2'-anhydro derivative 4 by selective deacetylation, mesylation, and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene. Cleavage of the 2,2'-anhydro ring in 4 with hydrogen bromide or hydrogen chloride led to the 2'-bromo (5) or 2'-chloro (6) derivative, respectively. Dehalogenation of 6 with tributylstannane and then debenzoylation gave 1-(2-deoxy-beta-D-arabino-hexofuranosyl)thymine (8). Isopropylidenation of 8 followed by mesylation, azide displacement, and deprotection gave 1-(3-azido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)thymine (12). Oxidation of 12 with Dowex 1 (IO4-) resin followed by reduction with Dowex 1 (BH4-) resin gave 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (AZT). Catalytic hydrogenation of 5 afforded a mixture of 1-(5,6-di-O-benzoyl-2,3-dideoxy-beta-D-erythro-hexofuranosyl)thymi ne (13) and 1-(3,5,6-tri-O-benzoyl-2-deoxy-beta-D-arabino-hexofuranosyl)thymin e (7). Reaction of 5 with a Cu/Zn couple gave 1-(5,6-di-O-benzoyl-2,3-dideoxy-beta-D-erythro-hex-2-enofuranosyl) thymine (15). 1-(2,3-Dideoxy-beta-D-erythro-hexofuranosyl)thymine (14) and 1-(2,3-dideoxy-beta-D-erythro-hex-2-enofuranosyl)thymine (16) were obtained by debenzoylation.","tracks":[{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":172},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":173,"end":384},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":385,"end":533},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":534,"end":657},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":658,"end":810},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":811,"end":973},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":974,"end":1177},"obj":"Sentence"},{"id":"TextSentencer_T8","span":{"begin":1178,"end":1297},"obj":"Sentence"},{"id":"TextSentencer_T9","span":{"begin":1298,"end":1453},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":172},"obj":"Sentence"},{"id":"T2","span":{"begin":173,"end":384},"obj":"Sentence"},{"id":"T3","span":{"begin":385,"end":533},"obj":"Sentence"},{"id":"T4","span":{"begin":534,"end":657},"obj":"Sentence"},{"id":"T5","span":{"begin":658,"end":810},"obj":"Sentence"},{"id":"T6","span":{"begin":811,"end":973},"obj":"Sentence"},{"id":"T7","span":{"begin":974,"end":1177},"obj":"Sentence"},{"id":"T8","span":{"begin":1178,"end":1297},"obj":"Sentence"},{"id":"T9","span":{"begin":1298,"end":1453},"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":"TextSentencer_T6","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T7","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T8","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T9","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"},{"subj":"T6","pred":"source","obj":"sentences"},{"subj":"T7","pred":"source","obj":"sentences"},{"subj":"T8","pred":"source","obj":"sentences"},{"subj":"T9","pred":"source","obj":"sentences"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"sentences","color":"#ab93ec","default":true}]}]}}