8-Methoxy Entecavir
8-Methoxy Entecavir is a purine nucleoside derivative featuring an 8-methoxy substitution on the bicyclic heteroaromatic core of the parent Entecavir molecule. This methylation at the 8-position of the guanine-like moiety introduces steric and electronic alterations, disrupting hydrogen bonding capacity critical for antiviral activity. The compound arises as a synthetic byproduct during Entecavir’s multi-step glycosylation process, particularly during purine ring functionalization. It serves as a high-purity reference standard for HPLC-based quantification of process-related impurities in Entecavir drug substance batches.
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IUPAC Name
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-8-methoxy-1H-purin-6-one
📝 Synonyms
8-Methoxy Entecavir
2349444-69-3
YJD4DV9LHH
Entecavir EP Impurity E
UNII-YJD4DV9LHH
8-Methoxy entecavir [USP]
8-Methoxy-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)guanine
2-Amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-8-methoxy-6H-purin-6-one
2-Amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-8-methoxy-1H-purin-6(9H)-one
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-8-methoxy-1H-purin-6-one
🔬 Chemical Identifiers
COC1=NC2=C(N1[C@H]3C[C@@H]([C@H](C3=C)CO)O)N=C(NC2=O)N
InChI=1S/C13H17N5O4/c1-5-6(4-19)8(20)3-7(5)18-10-9(15-13(18)22-2)11(21)17-12(14)16-10/h6-8,19-20H,1,3-4H2,2H3,(H3,14,16,17,21)/t6-,7-,8-/m0/s1
STXDLYSFRKKGPP-FXQIFTODSA-N
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