1997 Fiscal Year Final Research Report Summary
The Development of a Generally Synthetic Method of D-and L-Deoxyfuranose
| Project/Area Number |
07454198
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
物質変換
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| Research Institution | Kurashiki University of Science and the Arts |
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Principal Investigator |
SATO Tsuneo Kurashiki University of Science and the Arts, College of Science and Industrial Technology, Professor, 産業科学技術学部, 教授 (80183383)
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| Project Period (FY) |
1995 – 1997
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| Keywords | D-2,3-dideoxyribose / L-2,3-dideoxyribose / D-2-deoxyribose / D-3-deoxyribose / D-deoxysugar / L-deoxysugar / deoxy sugar having branched chain |
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| Research Abstract |
1.The reaction of the allyl anion derived from 1-methoxy-3-(phenylthio)-1-propene with benzyl(R)-glycidyl ether was provided(E,S)-6-benzyloxy-5-hydroxy-2-hexenal, which was then transformed into(E,S)-6-benzyloxy-5-tert-butyldimethylsiloxy-2-hexen-1-ol in two steps : (a)tert-BuMe_2SiCl ; (b)NaBH_4 Sharpless-Katsuki asymmetric epoxidation with D-diethyl tartrate followed by treatment with C_6H_5CH_2OH afforded(2R,3S,5S)-3,6-bis(benzyloxy)-5-tert-butyldimethylsiloxy-1,2-hexanediol. This compound was treated successively with 2-methoxypropene, tetrabutylammonium fluoride, H_2-Pd/C,NalO_4, and diluted HCl to give D-2-deoxyribofuranose.
2.(2S,3R,5S)-3,6-bis(benzyloxy)-5-tert-butyldimethylsiloxy-1,2-hexanediol was obtained using L-diethyl tartrate instead of D-diethyl tartrate in the method of 1.The vic-diol was treated successively Bu_4NF,NalO_4, and H_2-Pd/C to afford D-3-deoxyribofuranose.
3.D-3-Azido-2,3-dideoxyribofuronose was prepared using NaN_3 instead of C_6H_5CH_2OH in the method of 1.
4.D-2,3-Dideoxyribofuranose was obtained using LiAlH_4 instead of C_6H_5CH_2OH,on the other hand, L-2,3-dideoxyribofuranosewas produced by using(S)-glycidyl ether, L-diethyl tartrate, and LiAlH_4 according to the method of 1, respectively.
5.According to the method of 1, D-2-deoxy-4-methylribofuranose and D-2-deoxy-3-methylribofuranose were obtained using of 1-methoxy-2-methyl-3-(phenylthio)-1-propene and 1-methoxy-3-(phenylthio)-1-butene, respectively.
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