The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives
Treatment of D-ribose with chloral in the presence of acid catalyst gives 1,2-O-(S)-trichloroethylidene-α-D-ribofuranose (1) (β-ribochloralose). Some derivatives of this product (1) were synthesized to be used as an intermediate in carbohydrate chemistry. Tricyclic orthoester structure (3, 77%) was...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/748161 |
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| author | Kadir Ay Erkan Halay |
| author_facet | Kadir Ay Erkan Halay |
| author_sort | Kadir Ay |
| collection | DOAJ |
| description | Treatment of D-ribose with chloral in the presence of acid catalyst gives 1,2-O-(S)-trichloroethylidene-α-D-ribofuranose (1) (β-ribochloralose). Some derivatives of this product (1) were synthesized to be used as an intermediate in carbohydrate chemistry. Tricyclic orthoester structure (3, 77%) was obtained from the reaction of 1 with potassium t-butoxide. This novel orthoester is expected to be useful as a glycosyl donor in the formations of new ribofuranoside units. 3-O-Methyl-ribochloralose (5) was synthesized in 75% yield via the methylation of 1. 5-O-Tosyl-ribochloralose (6, 61%) was prepared with monotosylation reaction of 1. Treatment of 6 with NaN3 in DMF gives a 5-azido-5-deoxy-ribochloralose (7) in 77% yield. The azidosugar (7) was reduced to 5-amino-5-deoxy-ribochloralose (8, 72%) with triphenylphosphine according to Staudinger’s reduction procedure. |
| format | Article |
| id | doaj-art-9ff8326471a84ca79d2a2882a7e2927d |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
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| series | Journal of Chemistry |
| spelling | doaj-art-9ff8326471a84ca79d2a2882a7e2927d2025-02-03T05:58:43ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/748161748161The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some DerivativesKadir Ay0Erkan Halay1Department of Chemistry, Faculty of Arts and Sciences, Celal Bayar University, Campus of Muradiye, 45030 Manisa, TurkeyDepartment of Chemistry, Faculty of Arts and Sciences, Celal Bayar University, Campus of Muradiye, 45030 Manisa, TurkeyTreatment of D-ribose with chloral in the presence of acid catalyst gives 1,2-O-(S)-trichloroethylidene-α-D-ribofuranose (1) (β-ribochloralose). Some derivatives of this product (1) were synthesized to be used as an intermediate in carbohydrate chemistry. Tricyclic orthoester structure (3, 77%) was obtained from the reaction of 1 with potassium t-butoxide. This novel orthoester is expected to be useful as a glycosyl donor in the formations of new ribofuranoside units. 3-O-Methyl-ribochloralose (5) was synthesized in 75% yield via the methylation of 1. 5-O-Tosyl-ribochloralose (6, 61%) was prepared with monotosylation reaction of 1. Treatment of 6 with NaN3 in DMF gives a 5-azido-5-deoxy-ribochloralose (7) in 77% yield. The azidosugar (7) was reduced to 5-amino-5-deoxy-ribochloralose (8, 72%) with triphenylphosphine according to Staudinger’s reduction procedure.http://dx.doi.org/10.1155/2013/748161 |
| spellingShingle | Kadir Ay Erkan Halay The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives Journal of Chemistry |
| title | The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives |
| title_full | The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives |
| title_fullStr | The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives |
| title_full_unstemmed | The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives |
| title_short | The Newest Member of the Family of Chloralose: Synthesis of β-Ribochloralose and Some Derivatives |
| title_sort | newest member of the family of chloralose synthesis of β ribochloralose and some derivatives |
| url | http://dx.doi.org/10.1155/2013/748161 |
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