Description

((3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol is a high-purity nucleoside derivative extensively utilized in biochemical research and pharmaceutical development. With the molecular formula C₁₃H₁₇N₅O₄ and CAS number 362-75-4, this compound is a key intermediate in the synthesis of modified nucleosides and nucleotides. It is commonly referred to as 2′,3′-O-Isopropylideneadenosine, a protected form of adenosine that enhances stability during chemical transformations. This product is ideal for researchers investigating RNA/DNA analogs, antiviral agents, or enzyme inhibitors due to its well-defined structure and reactivity.

Available in various quantities with guaranteed ≥98% purity (HPLC/LCMS), this compound is supplied as a lyophilized powder under strict quality control to ensure batch-to-batch consistency. Store desiccated at -20°C for long-term stability. For research use only; not intended for diagnostic or therapeutic applications.

Properties

• CAS Number: 362-75-4
• Complexity: 439
• IUPAC Name: [(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• InChI: InChI=1S/C13H17N5O4/c1-13(2)21-8-6(3-19)20-12(9(8)22-13)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19H,3H2,1-2H3,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
• InChI Key: LCCLUOXEZAHUNS-WOUKDFQISA-N
• Exact Mass: 307.12805404
• Molecular Formula: C13H17N5O4
• Molecular Weight: 307.31
• SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C(N=CN=C43)N)CO)C
• Topological: 118
• Monoisotopic Mass: 307.12805404
• Synonyms: 2′,3′-O-Isopropylideneadenosine, 362-75-4, 21138-44-3, ((3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol, [(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methanol, MFCD00005756, [(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol, CHEMBL1321883, [(3aR,4R,6R)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol, 2′,3′-ISOPROPYLIDENE ADENOSINE, [(1R,2R,4R,5R)-4-(6-aminopurin-9-yl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oc t-2-yl]methan-1-ol, [(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol, Maybridge4_003341, 2,3-Isopropylideneadeosine, MLS002279959, SCHEMBL308385, SCHEMBL6754872, 2 inverted exclamation mark ,3 inverted exclamation mark -O-Isopropylideneadenosine, HMS2215M12, BDBM50228351, SBB002962, 2′,3′-O-Isopropylidene-D-adenosine, 2,3-O-(1-Methylethylidene)adenosine, AKOS015896812, AKOS015995298, DS-1175, NI05151, 2′,3′-O-Isopropylideneadenosine, 98%, NCGC00175949-01, SMR001318096, ST057077, DB-344450, EN300-1588517, BRD-K42211680-001-01-3, Z1741976708, 2 inverted exclamation marka,3 inverted exclamation marka-O-Isopropylideneadenosine, ((3 aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro furo[3,4-d][1,3]dioxol-4-yl)methanol, ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol, [(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl]methanol

This adenosine derivative serves as a crucial building block for synthesizing modified nucleosides in antiviral and anticancer drug discovery. It is employed in glycosylation reactions to study nucleotide metabolism and enzyme kinetics. Researchers also utilize it to develop fluorescent nucleoside analogs for probing nucleic acid structures. The isopropylidene protection group enables selective functionalization at the 5′-position while maintaining ribose ring integrity.

Safety and Hazards

GHS Hazard Statements

• Not Classified
• Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

Hazard Classes and Categories

• Not Classified

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.