30361-17-2

Basic information

• Product Name: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose
• Synonyms: 2,3,5-TRI-O-BENZOYL-2-C-METHYL-D-RIBOFURANOSE;2-C-Methyl-D-ribofuranose 2,3,5-tribenzoate;(3R,4R,5R)-5-((Benzoyloxy)methyl)-2-hydroxy-3-methyltetrahydrofuran-3,4-diyl dibenzoate;NGOREDWQTFTUTC-KXGJQKBVSA-N
• CAS NO: 30361-17-2
• Molecular Formula: C₂₇H₂₄O₈
• Molecular Weight: 476.479
• Mol File: 30361-17-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 617.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.35
• Refractive Index: 1.626
• PKA: 11.40±0.70(Predicted)
• CAS DataBase Reference: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose(30361-17-2)
• EPA Substance Registry System: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose(30361-17-2)

Safety Data

• Hazardous Substances Data: 30361-17-2(Hazardous Substances Data)

Usage

General Description

2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is a chemical compound that belongs to the class of ribofuranose derivatives. It consists of a ribofuranose sugar molecule that has been modified with three benzoyl groups and a methyl group at the C-2 position. 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose is often used as a building block in organic synthesis and medicinal chemistry due to its ability to serve as a protecting group for the hydroxyl groups in the ribofuranose molecule. It is commonly employed in the preparation of nucleosides, nucleotides, and other bioactive compounds. Additionally, it is used as a precursor in the synthesis of various natural and synthetic oligosaccharides, helping to create new compounds with potential biological activities.

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

• 2747-38-8 methyltrichlorotitanium 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 75-16-1 methylmagnesium bromide 
• 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 

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 articles and documents

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.

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.