2′,3′-O-isopropylidene inosine, CAS No. 2140-11-6

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2140-11-6

Catalog No. EBD37875

CAS 2140-11-6

Name 2′,3′-O-isopropylidene inosine

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Basic Information

Synonyms: 2',3'-o-isopropylideneinosine 2',3'-isopropylideneinosine 2',3'-o-isopropylidene-d-inosine 2'',3''-o-isopropylideneinosine,98.0+%(lc) 9-(2,3-o-isopropylidene-beta-d-ribofuranosyl)hypoxanthine 2'-o,3'-o-isopropylidene-2-deaminoguanosine 2'-o,3'-o-isopropylidene-6-hydroxy-6-deaminoadenosine 2'-o,3'-o-isopropylideneinosine 2',3'-O-(1-methylethylidene)inosine 9-[2,3-O-(1-methylethylidene)pentofuranosyl]-3,9-dihydro-6H-purin-6-one 2',3'-0-Isopropylideneinosine 2',3'-isopropylidene-inosine 2′,3′-O-isopropylideneinosine

Molecular Formula: C13H16N4O5

Molecular Weight: 308.29

MDL Number: MFCD00038002

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

Product Description:

2′,3′-O-Isopropylidene inosine is a chemically modified nucleoside derivative where the ribose sugar moiety of inosine is protected at the 2′ and 3′ hydroxyl positions with an isopropylidene (acetonide) group. This modification significantly alters the molecule's solubility and reactivity compared to the parent nucleoside, inosine. This compound serves as a crucial protected intermediate in nucleoside chemistry and medicinal chemistry research. Its primary application is in the synthesis of more complex nucleoside analogs, particularly antiviral and anticancer agents. The acetonide protection allows for selective functionalization at other positions of the nucleoside, such as the 5′-hydroxyl group, without affecting the sensitive cis-diol system of the ribose ring. It is a key building block for preparing prodrugs and modified nucleotides used in biochemical studies and drug discovery programs targeting viral polymerases and other nucleic acid-related enzymes. As a protected form of a naturally occurring nucleoside, it is a specialty chemical predominantly used in research and development settings rather than as a bulk pharmaceutical ingredient. Handling requires standard laboratory precautions for fine chemicals.

Physical Properties

Melting Point: 263-272°C

Boiling Point: 606.4 °C at 760 mmHg

Flash Point: 316.9 °C

Density: 1.89 g/cm3

Analytical Data

Appearance: White solid