PubMed:18768174 JSONTXT

{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":137},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":138,"end":303},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":304,"end":473},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":474,"end":686},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":687,"end":871},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":872,"end":971},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":972,"end":1162},"obj":"Sentence"},{"id":"TextSentencer_T8","span":{"begin":1163,"end":1335},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":137},"obj":"Sentence"},{"id":"T2","span":{"begin":138,"end":303},"obj":"Sentence"},{"id":"T3","span":{"begin":304,"end":473},"obj":"Sentence"},{"id":"T4","span":{"begin":474,"end":686},"obj":"Sentence"},{"id":"T5","span":{"begin":687,"end":871},"obj":"Sentence"},{"id":"T6","span":{"begin":872,"end":971},"obj":"Sentence"},{"id":"T7","span":{"begin":972,"end":1162},"obj":"Sentence"},{"id":"T8","span":{"begin":1163,"end":1335},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"tert-Butyldimethylsilyl O-protected chitosan and chitooligosaccharides: useful precursors for N-modifications in common organic solvents.\nAn efficient and chemoselective procedure for preparing highly organosoluble 3,6-di-O-tert-butyldimethylsilyl (TBDMS)-chitosan and chitooligosaccharides is reported. The selective modification of the chitooligosaccharides with 0.50 degree of N-acetylation was achieved by using TBDMSCl as the reagent in combination with DMF/imidazole. These protocols yielded partly TBDMS-substituted chitooligosaccharides that were subsequently reacted with TBDMSOTf in dichloromethane in order to silylate the remaining, more sterically hindered hydroxyl groups. In the case of the chitosan polymer, a mesylate salt of chitosan was silylated using TBDMSCl in DMSO, yielding full silylation of the hydroxyl groups without using N-protection groups. The silyl-protected polymers displayed excellent solubility in a number of common organic solvents. The 3,6-di-O-TBDMS-chitosan and chitooligosaccharides were reacted with acetic anhydride, and deprotected to obtain the corresponding N-acetyl derivatives (chitin and chitinoligosaccharide). Our results show that the readily prepared 3,6-di-O-TBDMS-chitosan and chitooligosaccharides are useful precursors for selective N-modifications in common organic solvents."}

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red":"arg1Of","subj":"EnjuParser_T154","obj":"EnjuParser_T153"},{"id":"EnjuParser_R156","pred":"arg2Of","subj":"EnjuParser_T156","obj":"EnjuParser_T154"},{"id":"EnjuParser_R157","pred":"arg1Of","subj":"EnjuParser_T155","obj":"EnjuParser_T156"},{"id":"EnjuParser_R158","pred":"arg2Of","subj":"EnjuParser_T157","obj":"EnjuParser_T156"},{"id":"EnjuParser_R159","pred":"arg1Of","subj":"EnjuParser_T156","obj":"EnjuParser_T158"},{"id":"EnjuParser_R160","pred":"arg2Of","subj":"EnjuParser_T160","obj":"EnjuParser_T158"},{"id":"EnjuParser_R161","pred":"arg1Of","subj":"EnjuParser_T160","obj":"EnjuParser_T159"},{"id":"EnjuParser_R162","pred":"arg1Of","subj":"EnjuParser_T160","obj":"EnjuParser_T161"},{"id":"EnjuParser_R163","pred":"arg2Of","subj":"EnjuParser_T163","obj":"EnjuParser_T161"},{"id":"EnjuParser_R164","pred":"arg1Of","subj":"EnjuParser_T163","obj":"EnjuParser_T162"},{"id":"EnjuParser_R165","pred":"arg1Of","subj":"EnjuParser_T163","obj":"EnjuParser_T164"},{"id":"EnjuParser_R166","pred":"arg2Of","subj":"EnjuParser_T167","obj":"EnjuParser_T164"},{"id":"EnjuParser_R167","pred":"arg1Of","subj":"EnjuParser_T167","obj":"EnjuParser_T165"},{"id":"EnjuParser_R168","pred":"arg1Of","subj":"EnjuParser_T167","obj":"EnjuParser_T166"}],"namespaces":[{"prefix":"_base","uri":"http://kmcs.nii.ac.jp/enju/"}],"text":"tert-Butyldimethylsilyl O-protected chitosan and chitooligosaccharides: useful precursors for N-modifications in common organic solvents.\nAn efficient and chemoselective procedure for preparing highly organosoluble 3,6-di-O-tert-butyldimethylsilyl (TBDMS)-chitosan and chitooligosaccharides is reported. The selective modification of the chitooligosaccharides with 0.50 degree of N-acetylation was achieved by using TBDMSCl as the reagent in combination with DMF/imidazole. These protocols yielded partly TBDMS-substituted chitooligosaccharides that were subsequently reacted with TBDMSOTf in dichloromethane in order to silylate the remaining, more sterically hindered hydroxyl groups. In the case of the chitosan polymer, a mesylate salt of chitosan was silylated using TBDMSCl in DMSO, yielding full silylation of the hydroxyl groups without using N-protection groups. The silyl-protected polymers displayed excellent solubility in a number of common organic solvents. The 3,6-di-O-TBDMS-chitosan and chitooligosaccharides were reacted with acetic anhydride, and deprotected to obtain the corresponding N-acetyl derivatives (chitin and chitinoligosaccharide). Our results show that the readily prepared 3,6-di-O-TBDMS-chitosan and chitooligosaccharides are useful precursors for selective N-modifications in common organic solvents."}

{"project":"GlyCosmos15-Glycan","denotations":[{"id":"T1","span":{"begin":1128,"end":1134},"obj":"Glycan"}],"attributes":[{"id":"A1","pred":"glycosmos_id","subj":"T1","obj":"https://glycosmos.org/glycans/show/G97099AY"},{"id":"A2","pred":"image","subj":"T1","obj":"https://api.glycosmos.org/wurcs2image/latest/png/binary/G97099AY"}],"text":"tert-Butyldimethylsilyl O-protected chitosan and chitooligosaccharides: useful precursors for N-modifications in common organic solvents.\nAn efficient and chemoselective procedure for preparing highly organosoluble 3,6-di-O-tert-butyldimethylsilyl (TBDMS)-chitosan and chitooligosaccharides is reported. The selective modification of the chitooligosaccharides with 0.50 degree of N-acetylation was achieved by using TBDMSCl as the reagent in combination with DMF/imidazole. These protocols yielded partly TBDMS-substituted chitooligosaccharides that were subsequently reacted with TBDMSOTf in dichloromethane in order to silylate the remaining, more sterically hindered hydroxyl groups. In the case of the chitosan polymer, a mesylate salt of chitosan was silylated using TBDMSCl in DMSO, yielding full silylation of the hydroxyl groups without using N-protection groups. The silyl-protected polymers displayed excellent solubility in a number of common organic solvents. The 3,6-di-O-TBDMS-chitosan and chitooligosaccharides were reacted with acetic anhydride, and deprotected to obtain the corresponding N-acetyl derivatives (chitin and chitinoligosaccharide). Our results show that the readily prepared 3,6-di-O-TBDMS-chitosan and chitooligosaccharides are useful precursors for selective N-modifications in common organic solvents."}