PubMed:12433462 JSONTXT

{"project":"GlyCosmos600-Glycan-Motif-Structure","denotations":[{"id":"T1","span":{"begin":37,"end":60},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"},{"id":"T2","span":{"begin":37,"end":60},"obj":"https://glytoucan.org/Structures/Glycans/G50850NI"},{"id":"T3","span":{"begin":152,"end":175},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"},{"id":"T4","span":{"begin":152,"end":175},"obj":"https://glytoucan.org/Structures/Glycans/G50850NI"},{"id":"T5","span":{"begin":177,"end":183},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos6-Glycan-Motif-Image","denotations":[{"id":"T1","span":{"begin":37,"end":60},"obj":"Glycan_Motif"},{"id":"T3","span":{"begin":152,"end":175},"obj":"Glycan_Motif"},{"id":"T5","span":{"begin":177,"end":183},"obj":"Glycan_Motif"}],"attributes":[{"id":"A1","pred":"image","subj":"T1","obj":"https://api.glycosmos.org/wurcs2image/0.10.0/png/binary/G81533KY"},{"id":"A2","pred":"image","subj":"T1","obj":"https://api.glycosmos.org/wurcs2image/0.10.0/png/binary/G50850NI"},{"id":"A3","pred":"image","subj":"T3","obj":"https://api.glycosmos.org/wurcs2image/0.10.0/png/binary/G81533KY"},{"id":"A4","pred":"image","subj":"T3","obj":"https://api.glycosmos.org/wurcs2image/0.10.0/png/binary/G50850NI"},{"id":"A5","pred":"image","subj":"T5","obj":"https://api.glycosmos.org/wurcs2image/0.10.0/png/binary/G81533KY"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos6-Glycan-Motif-Structure","denotations":[{"id":"T1","span":{"begin":37,"end":60},"obj":"https://glytoucan.org/Structures/Glycans/G50850NI"},{"id":"T2","span":{"begin":37,"end":60},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"},{"id":"T3","span":{"begin":152,"end":175},"obj":"https://glytoucan.org/Structures/Glycans/G50850NI"},{"id":"T4","span":{"begin":152,"end":175},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"},{"id":"T5","span":{"begin":177,"end":183},"obj":"https://glytoucan.org/Structures/Glycans/G81533KY"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos600-FMA","denotations":[{"id":"T1","span":{"begin":37,"end":60},"obj":"Body_part"},{"id":"T2","span":{"begin":152,"end":175},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"fma_id","subj":"T1","obj":"http://purl.org/sig/ont/fma/fma82788"},{"id":"A2","pred":"fma_id","subj":"T2","obj":"http://purl.org/sig/ont/fma/fma82788"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":83},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":84,"end":283},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":284,"end":662},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":663,"end":798},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":83},"obj":"Sentence"},{"id":"T2","span":{"begin":84,"end":283},"obj":"Sentence"},{"id":"T3","span":{"begin":284,"end":662},"obj":"Sentence"},{"id":"T4","span":{"begin":663,"end":798},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

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of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos15-Glycan","denotations":[{"id":"T1","span":{"begin":177,"end":183},"obj":"Glycan"}],"attributes":[{"id":"A1","pred":"glycosmos_id","subj":"T1","obj":"https://glycosmos.org/glycans/show/G76685HR"},{"id":"A2","pred":"image","subj":"T1","obj":"https://api.glycosmos.org/wurcs2image/latest/png/binary/G76685HR"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"Glycan-GlyCosmos","denotations":[{"id":"T1","span":{"begin":177,"end":183},"obj":"Glycan"}],"attributes":[{"id":"A1","pred":"glycosmos_id","subj":"T1","obj":"https://glycosmos.org/glycans/show/G76685HR"},{"id":"A2","pred":"image","subj":"T1","obj":"https://api.glycosmos.org/wurcs2image/latest/png/binary/G76685HR"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos15-UBERON","denotations":[{"id":"T1","span":{"begin":325,"end":334},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_2000106"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"GlyCosmos15-Sentences","blocks":[{"id":"T1","span":{"begin":0,"end":83},"obj":"Sentence"},{"id":"T2","span":{"begin":84,"end":283},"obj":"Sentence"},{"id":"T3","span":{"begin":284,"end":662},"obj":"Sentence"},{"id":"T4","span":{"begin":663,"end":798},"obj":"Sentence"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}

{"project":"Anatomy-UBERON","denotations":[{"id":"T1","span":{"begin":325,"end":334},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_2000106"}],"text":"Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.\nA general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule."}