CAS 7408-41-5

2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide

Description:

2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide is a chemical compound characterized by its azide functional group and a ribofuranosyl sugar moiety. The presence of three benzoyl groups indicates that the compound is heavily substituted, which can influence its solubility and reactivity. This compound is typically used in organic synthesis, particularly in the field of glycoscience, where it serves as a glycosyl donor in reactions to form glycosidic bonds. The azide group is notable for its ability to participate in click chemistry, allowing for the formation of triazoles when reacted with alkynes. The ribofuranosyl structure suggests that it is a derivative of ribose, a sugar that plays a crucial role in biological systems, particularly in RNA. The compound's stability, reactivity, and potential applications in bioconjugation and drug development make it of interest in both academic and industrial research settings. Proper handling and storage are essential due to the reactive nature of the azide group, which can pose safety hazards.

Formula: C₂₆H₂₁N₃O₇

InChI: InChI=1/C26H21N3O7/c27-29-28-23-22(36-26(32)19-14-8-3-9-15-19)21(35-25(31)18-12-6-2-7-13-18)20(34-23)16-33-24(30)17-10-4-1-5-11-17/h1-15,20-23H,16H2/t20-,21-,22-,23-/m1/s1

SMILES: c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@H]([C@H](N=[N+]=[NH-])O1)OC(=O)c1ccccc1)OC(=O)c1ccccc1

Synonyms:

• (2R,3R,4R,5R)-2-Azido-5-[(benzoyloxy)methyl]tetrahydrofuran-3,4-diyl dibenzoate (non-preferred name)
• (2R,3R,4R,5R)-2-azido-5-{[(phenylcarbonyl)oxy]methyl}tetrahydrofuran-3,4-diyl dibenzoate (non-preferred name)
• 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl azide
• benzoic acid (5-azido-3,4-dibenzoyloxy-2-oxolanyl)methyl ester
• 2,3,5-Tri-O-benzoyl-β-D-ribofuranosylazide
• 2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL AZIDE
• 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide USP/EP/BP
• 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl
• (2R,3R,4R,5R)-2-azido-5-(benzoyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate
• -D-ribofuranosylAzide
• 2,3,5-Tri-O-benzoyl-b-D-ribofuranosylazide

2,3,5-Tri-O-benzoyl-b-D-ribofuranosyl azide

CAS: 7408-41-5

Ref: 7W-GC7069

2,3,5-Tri-O-benzoyl-b-D-ribofuranosyl azide

CAS: 7408-41-5

2,3,5-Tri-O-benzoyl-b-D-ribofuranosyl azide (2,3,5-TRBA) is an antiviral agent that inhibits the synthesis of viral nucleic acid by targeting a glycosylation step in the synthesis of herpes simplex virus type 1 (HSV1). 2,3,5-TRBA has significant antiviral activity against HSV1 and other herpes viruses. This compound is also active against influenza A virus and vaccinia virus. 2,3,5-TRBA inhibits the enzyme triosephosphate isomerase (TPI), which catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde 3-phosphate. Inhibition of TPI leads to decreased glucose production in cells infected with herpes viruses. The acetonitrile used as a solvent in this reaction can be replaced by pyridine or DMF. The sulfonate group

Formula: C₂₆H₂₁N₃O₇

Purity: Min. 98 Area-%

Color and Shape: Powder

Molecular weight: 487.46 g/mol

Ref: 3D-MT06420