30361-17-2

Usage

Uses

Used in Organic Synthesis:
2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is used as a building block in organic synthesis for its ability to serve as a protecting group for the hydroxyl groups in the ribofuranose molecule. This property is crucial in the synthesis of complex organic compounds, where protecting specific functional groups is necessary to prevent unwanted reactions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is utilized as a key intermediate in the preparation of nucleosides and nucleotides, which are essential components of DNA and RNA. Its role in the synthesis of these bioactive compounds contributes to the development of new pharmaceuticals and therapeutic agents.
Used in the Synthesis of Oligosaccharides:
2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is also used as a precursor in the synthesis of various natural and synthetic oligosaccharides. Oligosaccharides are short chains of sugar molecules that play important roles in biological processes, such as cell recognition and signaling. The use of 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose in their synthesis helps create new compounds with potential biological activities, which can be explored for their therapeutic potential.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is used as a key component in the development of new drugs. Its role in the synthesis of nucleosides, nucleotides, and oligosaccharides makes it an essential building block for the creation of novel pharmaceutical compounds with potential therapeutic applications.

InChI:InChI=1/C27H24O8/c1-27(35-25(30)20-15-9-4-10-16-20)22(34-24(29)19-13-7-3-8-14-19)21(33-26(27)31)17-32-23(28)18-11-5-2-6-12-18/h2-16,21-22,26,31H,17H2,1H3/t21-,22-,26?,27-/m1/s1

Upstream product

• 7392-74-7 (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate 
• 98-88-4 benzoyl chloride 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 2747-38-8 methyltrichlorotitanium 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 
• 641571-44-0 (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 1345969-93-8 C₃₆H₃₆N₅O₁₀P 
• 1345969-94-9 diethyl (2-amino-9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-9H-purin-6-yl)phosphonate 
• 205171-10-4 2,6-dichloro-9-(2-C-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine 

Relevant academic research and scientific papers

Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

A variety of 2,6-modified purine 2′-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

2′-C-alkylribonucleosides: Design, synthesis, and conformation

Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.

A concise synthesis of 2'-C-methylribonucleosides

2'-C-methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-α-D-ribose with good overall yields.