Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose
This paper describes a convenient synthesis of 1,4-dideoxy-1,4-imino-D-ribitol (DRB) from D-ribose. L-Lyxonolactone, a key intermediate in this synthesis, was prepared by base-promoted hydrolysis of a 5-chlorinated D-ribonolactone derivative with inversion of configuration at the C-4 position. Cycli...
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| Main Authors: | , , , , |
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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/10.1155/2013/519415 |
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| author | Makoto Oba Shoi Kawaji Hironobu Kushima Takanori Sano Kozaburo Nishiyama |
| author_facet | Makoto Oba Shoi Kawaji Hironobu Kushima Takanori Sano Kozaburo Nishiyama |
| author_sort | Makoto Oba |
| collection | DOAJ |
| description | This paper describes a convenient synthesis of 1,4-dideoxy-1,4-imino-D-ribitol (DRB) from D-ribose. L-Lyxonolactone, a key intermediate in this synthesis, was prepared by base-promoted hydrolysis of a 5-chlorinated D-ribonolactone derivative with inversion of configuration at the C-4 position. Cyclization of the generated dimesylated L-lyxitol with benzylamine proceeded with another configurational inversion at C-4 to afford the D-ribo-configured pyrrolidine system, which upon deprotection gave DRB. |
| format | Article |
| id | doaj-art-fbffcffa7fa0499385c454019e70bd75 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-fbffcffa7fa0499385c454019e70bd752025-02-03T06:07:16ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/519415519415Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-RiboseMakoto Oba0Shoi Kawaji1Hironobu Kushima2Takanori Sano3Kozaburo Nishiyama4Department of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, JapanDepartment of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, JapanDepartment of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, JapanDepartment of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, JapanDepartment of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, JapanThis paper describes a convenient synthesis of 1,4-dideoxy-1,4-imino-D-ribitol (DRB) from D-ribose. L-Lyxonolactone, a key intermediate in this synthesis, was prepared by base-promoted hydrolysis of a 5-chlorinated D-ribonolactone derivative with inversion of configuration at the C-4 position. Cyclization of the generated dimesylated L-lyxitol with benzylamine proceeded with another configurational inversion at C-4 to afford the D-ribo-configured pyrrolidine system, which upon deprotection gave DRB.http://dx.doi.org/10.1155/2013/519415 |
| spellingShingle | Makoto Oba Shoi Kawaji Hironobu Kushima Takanori Sano Kozaburo Nishiyama Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose Journal of Chemistry |
| title | Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose |
| title_full | Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose |
| title_fullStr | Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose |
| title_full_unstemmed | Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose |
| title_short | Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose |
| title_sort | convenient synthesis of 1 4 dideoxy 1 4 imino d ribitol from d ribose |
| url | http://dx.doi.org/10.1155/2013/519415 |
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