Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
5 pages, 1 table, 1 scheme.
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2000-10-07
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Online Access: | http://hdl.handle.net/10261/17233 http://dx.doi.org/10.13039/501100008737 |
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dig-ipna-es-10261-172332019-11-13T08:48:56Z Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto Dirección General de Investigación Científica y Técnica, DGICT (España) Ministerio de Educación y Ciencia (España) 5 pages, 1 table, 1 scheme. The reaction of specifically protected alditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 6,8-dioxabicyclo[3.2.1]octane and 2,7-dioxabicyclo[2.2.1]heptane ring systems under neutral conditions. This methodology can be useful not only for the preparation of chiral synthons but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected uloses. This reaction could be considered to be an intramolecular glycosidation that proceeds through an oxycarbenium ion. This work was supported by Investigation Programme PB96-1461 of the Dirección General de Investigación Científica y Técnica. A.J.H. thanks the Ministerio de Education y Ciencia, Spain, for a fellowship. 2009-09-29T07:47:28Z 2009-09-29T07:47:28Z 2000-10-07 artículo http://purl.org/coar/resource_type/c_6501 Tetrahedron Letters 41(41): 7869-7873 (2000) 0040-4039 http://hdl.handle.net/10261/17233 10.1016/S0040-4039(00)01393-9 http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1016/S0040-4039(00)01393-9 none 2373 bytes 509639 bytes text/plain application/pdf Elsevier |
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5 pages, 1 table, 1 scheme. |
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Dirección General de Investigación Científica y Técnica, DGICT (España) |
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Dirección General de Investigación Científica y Técnica, DGICT (España) Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto |
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Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto |
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Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
author_sort |
Francisco, Cosme G. |
title |
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
title_short |
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
title_full |
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
title_fullStr |
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
title_full_unstemmed |
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
title_sort |
intramolecular hydrogen abstraction reaction in carbohydrate chemistry. synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems |
publisher |
Elsevier |
publishDate |
2000-10-07 |
url |
http://hdl.handle.net/10261/17233 http://dx.doi.org/10.13039/501100008737 |
work_keys_str_mv |
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1777669646071103488 |