Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose
Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00397881_v_n6_p893_Uhrig |
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todo:paper_00397881_v_n6_p893_Uhrig2023-10-03T14:49:54Z Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose Uhrig, M.L. Varela, O. Carbohydrates Chiral pool Enones Olefination Stereoselective synthesis Acetylation Benzene Carbonates Complexation Olefins Oxidation Deacetylation Enantiomers Enantiospecific synthesis Olefination Synthesis (chemical) 2 pyrone derivative arabinose article chemical reaction chemical structure chirality deacetylation enantiomer enantioselectivity olefination oxidation kinetics reaction analysis stereochemistry structure analysis synthesis Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-arabinopyranoside 3,4-thionocarbonates (7 and 14) from benzyl β-L- or β-D- arabinopyranosides (1 and 13). Trimethylphosphite-promoted olefination, followed by O-deacetylation and oxidation gave the optically pure enantiomeric enones 12 and 17 in about 50% overall yield. © Georg Thieme Verlag Stuttgart. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00397881_v_n6_p893_Uhrig |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Carbohydrates Chiral pool Enones Olefination Stereoselective synthesis Acetylation Benzene Carbonates Complexation Olefins Oxidation Deacetylation Enantiomers Enantiospecific synthesis Olefination Synthesis (chemical) 2 pyrone derivative arabinose article chemical reaction chemical structure chirality deacetylation enantiomer enantioselectivity olefination oxidation kinetics reaction analysis stereochemistry structure analysis synthesis |
| spellingShingle |
Carbohydrates Chiral pool Enones Olefination Stereoselective synthesis Acetylation Benzene Carbonates Complexation Olefins Oxidation Deacetylation Enantiomers Enantiospecific synthesis Olefination Synthesis (chemical) 2 pyrone derivative arabinose article chemical reaction chemical structure chirality deacetylation enantiomer enantioselectivity olefination oxidation kinetics reaction analysis stereochemistry structure analysis synthesis Uhrig, M.L. Varela, O. Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| topic_facet |
Carbohydrates Chiral pool Enones Olefination Stereoselective synthesis Acetylation Benzene Carbonates Complexation Olefins Oxidation Deacetylation Enantiomers Enantiospecific synthesis Olefination Synthesis (chemical) 2 pyrone derivative arabinose article chemical reaction chemical structure chirality deacetylation enantiomer enantioselectivity olefination oxidation kinetics reaction analysis stereochemistry structure analysis synthesis |
| description |
Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-arabinopyranoside 3,4-thionocarbonates (7 and 14) from benzyl β-L- or β-D- arabinopyranosides (1 and 13). Trimethylphosphite-promoted olefination, followed by O-deacetylation and oxidation gave the optically pure enantiomeric enones 12 and 17 in about 50% overall yield. © Georg Thieme Verlag Stuttgart. |
| format |
JOUR |
| author |
Uhrig, M.L. Varela, O. |
| author_facet |
Uhrig, M.L. Varela, O. |
| author_sort |
Uhrig, M.L. |
| title |
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| title_short |
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| title_full |
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| title_fullStr |
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| title_full_unstemmed |
Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| title_sort |
enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose |
| url |
http://hdl.handle.net/20.500.12110/paper_00397881_v_n6_p893_Uhrig |
| work_keys_str_mv |
AT uhrigml enantiospecificsynthesisofbothenantiomersof2benzyloxydihydropyran3onesfromarabinose AT varelao enantiospecificsynthesisofbothenantiomersof2benzyloxydihydropyran3onesfromarabinose |
| _version_ |
1807319367591919616 |