Description

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (CAS No. 112921-00-3) is a high-purity, synthetic nucleoside derivative with the molecular formula C₁₃H₁₈N₆O₆S. This compound features a modified adenosine core with a sulfamate group at the 5′-position and a 2′,3′-O-isopropylidene protecting group, enhancing its stability for research applications. It is supplied as a lyophilized solid with ≥95% purity (HPLC), ensuring reproducibility in biochemical and pharmaceutical studies. Ideal for investigating nucleoside metabolism, enzyme inhibition, and prodrug development, this product is rigorously characterized by ¹H/¹³C NMR, LC-MS, and elemental analysis. Store at -20°C under inert conditions to maintain stability.

Properties

• CAS Number: 112921-00-3
• Complexity: 644
• 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]methyl sulfamate
• InChI: InChI=1S/C13H18N6O6S/c1-13(2)24-8-6(3-22-26(15,20)21)23-12(9(8)25-13)19-5-18-7-10(14)16-4-17-11(7)19/h4-6,8-9,12H,3H2,1-2H3,(H2,14,16,17)(H2,15,20,21)/t6-,8-,9-,12-/m1/s1
• InChI Key: PCKRSJUZRCXCIR-WOUKDFQISA-N
• Exact Mass: 386.10085349
• Molecular Formula: C13H18N6O6S
• Molecular Weight: 386.39
• SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C(N=CN=C43)N)COS(=O)(=O)N)C
• Topological: 175
• Monoisotopic Mass: 386.10085349
• Synonyms: 112921-00-3, ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate, adenosine, 2′,3′-o-(1-methylethylidene)-, 5′-sulfamate, Furo[3,4-d]-1,3-dioxole, adenosine deriv., SCHEMBL2292456, Furo[3,4-d]-1,3-dioxole,adenosinederiv., CS-0039600, C13611

Application

This adenosine-derived sulfamate is primarily used in medicinal chemistry research as a precursor for prodrug development targeting kinase and sulfatase enzymes. Its isopropylidene-protected ribose moiety facilitates selective modification studies in nucleoside chemistry. Researchers employ it to investigate adenosine receptor interactions and nucleotide analog metabolism in cell-based assays.

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