Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons
10 pages, 3 tables, 3 schemes.-- PMID: 11597215 [PubMed].-- Printed version published Oct 19, 2001.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0156565
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American Chemical Society
2001-09-18
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dig-ipna-es-10261-167602019-11-18T08:26:56Z Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons Francisco, Cosme G. León, Elisa I. Martín, Ángeles Moreno, Pilar Rodríguez Morales, María S. Suárez, Ernesto Dirección General de Investigación Científica y Técnica, DGICT (España) Ministerio de Educación y Ciencia (España) 10 pages, 3 tables, 3 schemes.-- PMID: 11597215 [PubMed].-- Printed version published Oct 19, 2001.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0156565 A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1−C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using this methodology, interesting four- and five-carbon building blocks for natural products synthesis possessing d-erythritol, d-threitol, d-xylitol, and d-arabinitol stereochemistry have been prepared. The synthesis of 1,2-O-isopropylidene-β-l-threose (40) and 1-acetamido-2,4,5-tri-O-acetyl-d-arabinitol (50) have also been achieved from 1,2:5,6-di-O-isopropylidene-β-d-glucofuranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-d-glucopyranose, respectively. This work was supported by the Investigation Program No. PB96-1461 of the Dirección General de Investigación Científica y Técnica, Spain. P.M. and A.M. thank the Ministerio de Educación y Ciencia, Spain, for a fellowship and a contract under the program Acciones para la Incorporación a España de Doctores y Tecnólogos, respectively. 2009-09-09T07:22:09Z 2009-09-09T07:22:09Z 2001-09-18 artículo http://purl.org/coar/resource_type/c_6501 Journal of Organic Chemistry 66(21): 6967-6976 (2001) 0022-3263 http://hdl.handle.net/10261/16760 10.1021/jo0156565 http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1021/jo0156565 none 2373 bytes 682237 bytes text/plain application/pdf American Chemical Society |
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10 pages, 3 tables, 3 schemes.-- PMID: 11597215 [PubMed].-- Printed version published Oct 19, 2001.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0156565 |
| author2 |
Dirección General de Investigación Científica y Técnica, DGICT (España) |
| author_facet |
Dirección General de Investigación Científica y Técnica, DGICT (España) Francisco, Cosme G. León, Elisa I. Martín, Ángeles Moreno, Pilar Rodríguez Morales, María S. Suárez, Ernesto |
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artículo |
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Francisco, Cosme G. León, Elisa I. Martín, Ángeles Moreno, Pilar Rodríguez Morales, María S. Suárez, Ernesto |
| spellingShingle |
Francisco, Cosme G. León, Elisa I. Martín, Ángeles Moreno, Pilar Rodríguez Morales, María S. Suárez, Ernesto Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| author_sort |
Francisco, Cosme G. |
| title |
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| title_short |
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| title_full |
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| title_fullStr |
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| title_full_unstemmed |
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons |
| title_sort |
reductive fragmentation of carbohydrate anomeric alkoxy radicals. synthesis of alditols with potential utility as chiral synthons |
| publisher |
American Chemical Society |
| publishDate |
2001-09-18 |
| url |
http://hdl.handle.net/10261/16760 http://dx.doi.org/10.13039/501100008737 |
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