β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose)
Benzoylation of L-rhamnono-1,5-lactone (1) with an excess of benzoyl chloride and pyridine for 16 h afforded 2,4-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone (2). Catalytic hydrogenation of 2 was stereoselective and gave crystalline 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lacton...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v70_n1_p27_Varela |
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todo:paper_00086215_v70_n1_p27_Varela2023-10-03T14:07:38Z β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) Varela, O.J. Cirelli, A.F. De Lenderkremer, R.M. Benzoylation of L-rhamnono-1,5-lactone (1) with an excess of benzoyl chloride and pyridine for 16 h afforded 2,4-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone (2). Catalytic hydrogenation of 2 was stereoselective and gave crystalline 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone (3). Reduction of the lactone 3 with disiamylborane afforded 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexopyranose (4) which, on debenzoylation, gave 3,6-dideoxy-L-arabino-hexose (ascarylose) (7) in good overall yield. The sugar was identified as the corresponding alditol (ascarylitol) and by convertion into methyl 3,6-dideoxy-α-L-arabino-hexopyranoside (methyl ascaryloside, 6). © 1979. Fil:Varela, O.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v70_n1_p27_Varela |
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Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
Benzoylation of L-rhamnono-1,5-lactone (1) with an excess of benzoyl chloride and pyridine for 16 h afforded 2,4-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone (2). Catalytic hydrogenation of 2 was stereoselective and gave crystalline 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone (3). Reduction of the lactone 3 with disiamylborane afforded 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexopyranose (4) which, on debenzoylation, gave 3,6-dideoxy-L-arabino-hexose (ascarylose) (7) in good overall yield. The sugar was identified as the corresponding alditol (ascarylitol) and by convertion into methyl 3,6-dideoxy-α-L-arabino-hexopyranoside (methyl ascaryloside, 6). © 1979. |
| format |
JOUR |
| author |
Varela, O.J. Cirelli, A.F. De Lenderkremer, R.M. |
| spellingShingle |
Varela, O.J. Cirelli, A.F. De Lenderkremer, R.M. β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| author_facet |
Varela, O.J. Cirelli, A.F. De Lenderkremer, R.M. |
| author_sort |
Varela, O.J. |
| title |
β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| title_short |
β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| title_full |
β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| title_fullStr |
β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| title_full_unstemmed |
β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) |
| title_sort |
β-elimination in aldonolactones. synthesis of 3,6-dideoxy l-arabino-hexose (ascarylose) |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v70_n1_p27_Varela |
| work_keys_str_mv |
AT varelaoj beliminationinaldonolactonessynthesisof36dideoxylarabinohexoseascarylose AT cirelliaf beliminationinaldonolactonessynthesisof36dideoxylarabinohexoseascarylose AT delenderkremerrm beliminationinaldonolactonessynthesisof36dideoxylarabinohexoseascarylose |
| _version_ |
1807324343107059712 |