PubMed:2379204 JSONTXT

{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":148},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":149,"end":642},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":643,"end":899},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":900,"end":1185},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":1186,"end":1410},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":1411,"end":1653},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":148},"obj":"Sentence"},{"id":"T2","span":{"begin":149,"end":642},"obj":"Sentence"},{"id":"T3","span":{"begin":643,"end":899},"obj":"Sentence"},{"id":"T4","span":{"begin":900,"end":1185},"obj":"Sentence"},{"id":"T5","span":{"begin":1186,"end":1410},"obj":"Sentence"},{"id":"T6","span":{"begin":1411,"end":1653},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Synthesis and ring-opening reactions of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranoside.\nTreatment of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside (1) with 2.3 mol. equiv. of diethyl azodicarboxylate (DEAD) and 1.3 mol. equiv. of triphenylphosphine (TPP) in toluene gave a mixture of 3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (2, 55%) and 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (3, 35%). Compound 3 was also synthesised from 6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-alpha-D-galactopyrano syl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside by epoxidation with DEAD-TPP and removal of the silyl ether group with tetrabutylammonium fluoride. The SN2 reactions of 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (5) with fluoride, chloride, bromide, iodide, and azide ions gave the corresponding 4'-derivatives 10, 12, 14, 18, and 20, respectively. Reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-bromo-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (15) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (16). A similar reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-azido-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (21) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-amino-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (22)."}

{"project":"PubmedHPO","denotations":[{"id":"T1","span":{"begin":307,"end":311},"obj":"HP_0000365"},{"id":"T2","span":{"begin":820,"end":824},"obj":"HP_0000365"}],"text":"Synthesis and ring-opening reactions of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranoside.\nTreatment of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside (1) with 2.3 mol. equiv. of diethyl azodicarboxylate (DEAD) and 1.3 mol. equiv. of triphenylphosphine (TPP) in toluene gave a mixture of 3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (2, 55%) and 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (3, 35%). Compound 3 was also synthesised from 6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-alpha-D-galactopyrano syl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside by epoxidation with DEAD-TPP and removal of the silyl ether group with tetrabutylammonium fluoride. The SN2 reactions of 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (5) with fluoride, chloride, bromide, iodide, and azide ions gave the corresponding 4'-derivatives 10, 12, 14, 18, and 20, respectively. Reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-bromo-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (15) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (16). A similar reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-azido-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (21) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-amino-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (22)."}

{"project":"Anatomy-UBERON","denotations":[{"id":"T1","span":{"begin":19,"end":26},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_0004111"}],"text":"Synthesis and ring-opening reactions of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranoside.\nTreatment of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside (1) with 2.3 mol. equiv. of diethyl azodicarboxylate (DEAD) and 1.3 mol. equiv. of triphenylphosphine (TPP) in toluene gave a mixture of 3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (2, 55%) and 4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (3, 35%). Compound 3 was also synthesised from 6-O-tert-butyldiphenylsilyl-4-chloro-4-deoxy-alpha-D-galactopyrano syl 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranoside by epoxidation with DEAD-TPP and removal of the silyl ether group with tetrabutylammonium fluoride. The SN2 reactions of 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-alpha-D-galactopyranosyl 3,4-anhydro-1,6-dichloro-1,6-dideoxy-beta-D-lyxo-hexulofuranosi de (5) with fluoride, chloride, bromide, iodide, and azide ions gave the corresponding 4'-derivatives 10, 12, 14, 18, and 20, respectively. Reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-bromo-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (15) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (16). A similar reduction of 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-azido-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (21) gave 4-chloro-4-deoxy-alpha-D-galactopyranosyl 4-amino-1,6-dichloro-1,4,6-trideoxy-beta-D-fructofuranoside (22)."}