21047-89-2

Basic information

• Product Name: Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-
• Synonyms: Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-;N2-isobutyrylguanine (monohydrate);N-(6,7-Dihydro-6-oxo-1H-purin-2-yl)-2-methylpropanamide;"PropanaMide, N-(6,9-dihydro-6-oxo-1H-purin-2-yl)-2-Methyl-;N-(6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyraMide;N-(6-Oxo-6,7-dihydro-1H-purin-2-yl)isobutyraMide;N2- isobuttyryl guanine;2-N-isobutyrylguanine
• CAS NO: 21047-89-2
• Molecular Formula: C₉H₁₁N₅O₂
• Molecular Weight: 221.22
• Product Categories: Naphthyridine,Quinoline
• Mol File: 21047-89-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: >300 °C
• Appearance: /
• Density: 1.61 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.15±0.20(Predicted)
• CAS DataBase Reference: Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-(21047-89-2)
• EPA Substance Registry System: Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-(21047-89-2)

Safety Data

• Hazardous Substances Data: 21047-89-2(Hazardous Substances Data)

Usage

Uses

N-(6,7-Dihydro-6-oxo-1H-purin-2-yl)-2-methylpropanamide is applied in the enzymic transglycosylation of purine nucleobases in synthesis of purine nucleosides.

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 79-30-1 isobutyryl chloride 
• 97-72-3 2-Methylpropionic anhydride 
• 1468-39-9 Isovaleric anhydride 
• 73-40-5 guanine 
• 73-40-5 guanine 

Downstream Products

• 185610-53-1 N²-(isobutyryl-O⁶-diphenylcarbamoyl)guanine 
• 902452-68-0 7-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxy-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-N-isobutyrylguanine 
• 145593-92-6 N⁹-(2',4',6'-Tri-O-benzoyl-3'-deoxy-β-D-glucopyranosyl)guanin 
• 145610-61-3 N⁷-(2',4',6'-Tri-O-benzoyl-3'-deoxy-β-D-glucopyranosyl)guanin 
• 145593-93-7 N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin 
• 133272-03-4 9-ethyl-6-hydroxy-2-isobutyramidopurin 
• 133294-70-9 9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)-6-hydroxy-2-isobutyramidopurin 
• 133272-04-5 Benzoic acid (2S,3S,4R,5R)-3-(ethoxy-hydroxy-phosphorylmethyl)-4-hydroxy-5-(6-hydroxy-2-isobutyrylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester; compound with triethyl-amine 
• 133272-05-6 C₂₆H₃₁N₅O₁₀P^(1-)*Na⁽¹⁺⁾ 
• 206055-59-6 N-[9-[(2R,3R,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide 
• 182625-84-9 (R)-9-(3-(4,4′-dimethoxytrityloxy)-2-hydroxypropyl)-N2-isobutyrylguanine 
• 182625-67-8 (S)-9-(3-(4,4′-dimethoxytrityloxy)-2-hydroxypropyl)-N2-isobutyrylguanine 

Relevant articles and documents

Observation of two N2-isobutyrylguanine tautomers by NMR spectroscopy

N2-Isobutyrylguanine was prepared by treatment of guanine with isobutyryl chloride. Two tautomers, 1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6- one and 1,9-dihydro-2-(isobutyroyl)amino-6H-purin-6-one, were identified in almost 1: 1 ratio in dichloromethane-dimethyl sulfoxide (1: 1 v/v) by NMR spectroscopy. By using the selective-inversion experiments, enthalpy, entropy, and free energy for activation were determined. This work represents the first report of guanine tautomers observed directly by NMR spectroscopy. Copyright

CYCLOPENTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS

Described herein are cyclopentyl nucleoside analogs, pharmaceutical compositions that include one or more cyclopentyl nucleoside analogs and methods of using the same to treat HBV, HDV and/or HIV.

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.