1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose - CAS 58381-23-0
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1.Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands.
Lee HW1, Choi WJ2, Jacobson KA3, Jeong LS1. Bull Korean Chem Soc. 2011;32(5):1620-1624.
Homologated analogues 3a and 3b of potent and selective A3 adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (4) via Co2(CO)8-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues 3a and 3b did not show significant binding affinities at three subtypes of adenosine receptors, indicating that free rotation, resulting from homologation, induced unfavorable interactions in the binding site of the receptor maybe due to the presence of many conformations.
2.Synthesis of α-L-threose nucleoside phosphonates via regioselective sugar protection.
Dumbre SG1, Jang MY, Herdewijn P. J Org Chem. 2013 Jul 19;78(14):7137-44. doi: 10.1021/jo400907g. Epub 2013 Jul 3.
A new synthesis route to α-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.
3.Novel method of synthesis of 5''-phosphate 2'-O-ribosyl-ribonucleosides and their 3'-phosphoramidites.
Chmielewski MK, Markiewicz WT1. Molecules. 2013 Nov 29;18(12):14780-96. doi: 10.3390/molecules181214780.
Synthesis of 5''-phosphate 2'-O-ribosylribonucleosides [Nr(p)] of four common ribonucleosides, and 3'-phosphoramidites of 5''-phosphate 2'-O-ribosyladenosine and 2'-O-ribosylguanosine using the H-phosphonate chemistry is described. An additional ring protected by benzoyl groups was incorporated into the main ribosyl ring in the reaction with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of SnCl4. The obtained 2'-O-ribosylribonucleosides (Nr) were applied in the subsequent transformations with selective deprotection. Ethanolamine was applied as a very convenient reagent for selective removal of benzoyl groups. Additionally, the tetraisopropyldisiloxane-1,3-diyl (TIPDSi) group was found to be stable under these deprotection conditions. Thus, the selectively deprotected 5''-hydroxyl group of Nr was transformed into an H-phosphonate monoester which was found to be stable under the following conditions: the removal of the TIPDSi group with triethylammonium fluoride and the dimethoxytritylation of the 5''-hydroxyl function.
4.Synthesis, spectral characterization, and biological activity of some new substituted 10H-phenothiazines, its ribofuranosides, and sulfones.
Gautam N1, Ajmera N, Gupta S, Gautam DC. Nucleosides Nucleotides Nucleic Acids. 2010 Mar;29(3):178-89. doi: 10.1080/15257771003708538.
This article describes the synthesis of new substituted 10 H-phenothiazines by Smiles rearrangement. These compounds are then used as a base to form ribofuranosides by treating them with a sugar (1-O-acetyl-2,3,5-tri-O-benzoyl-beta-ribofuranose). On oxidation with hydrogen peroxide in glacial acetic acid, these phenothiazines yield their sulfones. These compounds are screened for antioxidant and antimicrobial activity and their structure has been established by elemental analysis and spectroscopic data.
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CAS 58381-23-0 1-O-Acetyl-2,3,5-tri-O-benzyl-D-ribofuranose

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