1-O-Acetyl-2,3,5-tri-O-benzoyl-b-L-ribofuranose - CAS 3080-30-6
Product Name:
b-L-Ribofuranose 1-acetate 2,3,5-tribenzoate
CAS Number:
Molecular Weight:
Molecular Formula:
Chemical Structure
CAS 3080-30-6 1-O-Acetyl-2,3,5-tri-O-benzoyl-b-L-ribofuranose

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Reference Reading

1.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.
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.Synthesis and antimicrobial activities of novel biologically active heterocycles: 10h-phenothiazines, their ribofuranosides, and sulfone derivatives.
Dixit Y1, Dixit R, Gautam N, Gautam DC. Nucleosides Nucleotides Nucleic Acids. 2009 Nov;28(11):998-1006. doi: 10.1080/15257770903362206.
This article deals with the synthesis and antimicrobial activity of a series of novel substituted 10H-phenothiazines, their ribofuranosides, and sulfone derivatives. 10H-Phenothiazines were prepared by Smiles rearrangement. These prepared phenothiazines were used as the base to prepare ribofuranosides by treatment with sugar (1-O-acetyl-2,3,5-tri-O-benzoylribofuranose). Sulfone derivatives were prepared by the oxidation of 10H-phenothiazines. The structure of the synthesized compounds was established by elemental analysis and spectroscopic data.
4.Malonylated glycerolipids from the glandular trichome exudate of Ceratotheca triloba.
Ohkawa A1, Sakai T, Ohyama K, Fujimoto Y. Chem Biodivers. 2012 Aug;9(8):1611-7. doi: 10.1002/cbdv.201200097.
Chemical investigation of the glandular trichome exudate from Ceratotheca triloba (Pedaliaceae) led to the identification of nine 1-O-acetyl-2-O-[(R)-3-acetyloxy-fatty acyl]-3-O-malonylglycerols. Among these, 1-O-acetyl-2-O-[(R)-3-acetyloxyicosanoyl]-3-O-malonylglycerol (7) was the most abundant constituent (41%), followed by 1-O-acetyl-2-O-[(R)-(3-acetyloxyoctadecanoyl)-3-O-malonylglycerol (2; 21%). Compounds having iso- and anteiso-type structures in the 3-acetyloxy-fatty acyl groups in the fatty acyl moiety were also characterized as minor constituents. This is the first report of the isolation of malonylated glycerolipids as natural products.