(2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate, CAS No. 13035-61-5

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13035-61-5

Catalog No. EBD141994

CAS 13035-61-5

Name (2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate

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Basic Information

Synonyms: Beta-D-Ribofuranose1,2,3,5-tetraacetate 1,2,3,5-Tetra-O-acetyl-D-ribofuranose 1,2,3,5-tetraacetyl-beta-D-ribose 1,2,3,5-tetraacetyl-beta-D-ribofuranose Tetraacetylribofuranose 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose 1,2,3,5-tetra-O-acetylpentofuranose [(2S,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl]acetate 1,2,3,5-Tetra-O-Acetyl-D-Ribose 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose beta-D-Ribofuranose?1,2,3,5-tetraacetate β-D-Ribofuranose1,2,3,5-tetraacetate tetraacetylribose tetraacetyl-beta-d-ribofuranose tetra-o-acetyl-b-d-ribofuranose tetra-o-acetyl-beta-d-ribofuranose ribofuranosetetraacetate beta-d-ribofuranose1,2,3,5-tetra-o-acetate β-D-ribofuranosetetraacetate (2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanylacetate

Molecular Formula: C13H18O9

Molecular Weight: 318.28

MDL Number: MFCD00005358

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides

Product Description:

(2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate, commonly known as 1,2,3,5-tetra-O-acetyl-ж┬-D-ribofuranose, is a fully acetylated derivative of D-ribofuranose. Its structure features a tetrahydrofuran ring with four acetate protecting groups at the 1, 2, 3, and 5 positions, rendering it a stable, crystalline intermediate. This compound serves as a pivotal synthetic building block in nucleoside chemistry, primarily used for the preparation of ribonucleosides and modified nucleoside analogs. It acts as a glycosyl donor in Vorbrи╣ggen-type glycosylation reactions, enabling the coupling with nucleobases to form protected nucleosides, which are further deprotected to yield antiviral or anticancer drug candidates (e.g., ribavirin, remdesivir intermediates). Additionally, it is widely employed in the synthesis of oligonucleotide precursors, RNA probes, and bioactive small molecules. Its high purity and stability make it a standard reagent in pharmaceutical R&D and large-scale manufacturing of nucleoside-based therapeutics.

Physical Properties

Melting Point: 81-83 °C(lit.)

Boiling Point: 385.6 °C at 760 mmHg

Flash Point: 168.5 °C

Density: 1.29 g/cm3

Refractivity: -14.5 ° (C=5, MeOH)

Analytical Data

Appearance: white to almost white crystalline powder