2′,3′,5′-Tri-O-acetylinosine
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2′,3′,5′-Tri-O-acetylinosine
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CAS No:
3181-38-2
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Formula:
C16H18N4O8
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Chemical Name:
2′,3′,5′-Tri-O-acetylinosine
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Synonyms:
Inosine,2′,3′,5′-triacetate;2′,3′,5′-Triacetylinosine;2′,3′,5′-Tri-O-acetylinosine;NSC 66386;Chembridge 5141605;288154-83-6;307942-38-7
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CAS No:
2′,3′,5′-Tri-O-acetylinosine Basic Attributes
394.33600
394.34
221-669-7
97105|90329|83296|66386
29349990
Characteristics
151.70000
1.62 g/cm3
241 °C @ Solvent: Ethanol
620.7ºC at 760 mmHg
329.2ºC
1.727
-20ºC
2′,3′,5′-Tri-O-acetylinosine Use and Manufacturing
To a suspension of inosine (1 Og, 37. 3mmol) and catalytic DMAP in MeCN (60mL) was added Et3N (20mL, 143mmol) and acetic anhydride (12.5mL) and the resulting solution was stirred for 1h at ambient temperature before the addition of MeOH (5mL). After stirring for 5mins, the solution was concentrated in vacuo to yield a white solid which was washed with isopropyl alcohol to afford triacetoxy inosine (12. 1g, 82percent).General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.
An intermediate used for the synthesis of 6-substituted purine ribosides
Computed Properties
Molecular Weight:394.34
XLogP3:-1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:8
Exact Mass:394.11246355
Monoisotopic Mass:394.11246355
Topological Polar Surface Area:147
Heavy Atom Count:28
Complexity:698
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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