- A practical synthesis of L-FMAU from L-arabinose
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A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.
- Du, Jinfa,Choi, Yongseok,Lee, Kyeong,Chun, Byoung K.,Hong, Joon H.,Chu, Chung K.
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- L-nucleoside compounds and application thereof
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The invention discloses L-nucleoside compounds having the structure characteristic represented by the formula (I) or pharmaceutically acceptable salts thereof, and belongs to the technical field of pharmaceutical chemistry. The compounds can inhibit the activity of RNA viral polymerase, so the compounds can be used as potential drugs for prevention and treatment of infection of RNA viruses such as HCV, influenza virus, HRV (rhinovirus), RSV, Ebola virus, dengue virus, intestinal virus and the like.
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- A solid-phase approach to novel purine and nucleoside analogs
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This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbrueggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective oxidation-reduction procedure of the 2-OH group. Some compounds exhibited moderate activity against HIV-1 in PBM cells.
- Chang, Junbiao,Dong, Chunhong,Guo, Xiaohe,Hu, Weidong,Cheng, Senxiang,Wang, Qiang,Chen, Rongfeng
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p. 4760 - 4766
(2007/10/03)
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- Synthesis and testing of new modified nucleosides
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New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-c and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analogues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.
- Jung, Michael E.,Nichols, Christopher J.,Kretschik, Oliver,Xu, Yue
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p. 541 - 546
(2007/10/03)
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- Efficient syntheses of L-ribose and 2-deoxy L-ribose from D-ribose and L-arabinose
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Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14.
- Jung, Michael E.,Xu, Yue
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p. 4199 - 4202
(2007/10/03)
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