Description

(2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo(6.4.0.0,2,6)dodeca-8,11-dien-10-one (CAS: 22423-26-3) is a highly specialized nucleoside derivative with a complex tricyclic structure. This compound, also known as 2,2′-Anhydro-5-methyluridine, is characterized by its unique furo-oxazolo-pyrimidinone scaffold, making it valuable for biochemical and pharmaceutical research. With a molecular formula of C₁₀H₁₂N₂O₅, it exhibits high purity (>98%) and is supplied as a white to off-white crystalline powder. Its stability under controlled conditions (−20°C, dry atmosphere) ensures reliable performance in synthetic applications. Researchers utilize this compound in nucleoside analog synthesis, antiviral drug development, and RNA modification studies due to its structural similarity to thymidine.

Properties

• CAS Number: 22423-26-3
• Complexity: 432
• IUPAC Name: (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one
• InChI: InChI=1S/C10H12N2O5/c1-4-2-12-9-7(6(14)5(3-13)16-9)17-10(12)11-8(4)15/h2,5-7,9,13-14H,3H2,1H3/t5-,6-,7+,9-/m1/s1
• InChI Key: WLLOAUCNUMYOQI-JAGXHNFQSA-N
• Exact Mass: 240.07462149
• Molecular Formula: C10H12N2O5
• Molecular Weight: 240.21
• SMILES: CC1=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)OC2=NC1=O
• Topological: 91.6
• Monoisotopic Mass: 240.07462149
• Synonyms: (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.0,2,6]dodeca-8,11-dien-10-one, (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo(6.4.0.0,2,6)dodeca-8,11-dien-10-one, 898-613-9, 22423-26-3, 2,2′-Anhydro-5-methyluridine, 2,2′-Anhydrothymidine, GQZ99GWR3T, (2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-7-methyl-3,3a-dihydro-2H-furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-one, TK-112690, 6H-Furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-,(2R,3R,3aS,9aR)-, 2,2′-O-Anhydro-5-methyluridine, (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one, 2,2′-Anhydro-athy, 2,2′-Cyclothymidine, 6H-FURO(2′,3′:4,5)OXAZOLO(3,2-A)PYRIMIDIN-6-ONE, 2,3,3A,9A-TETRAHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-7-METHYL-, (2R,3R,3AS,9AR)-, 6H-Furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R,3R,3aS,9aR)-, UNII-GQZ99GWR3T, 2,2′-Anhydro-1-beta-arabinofuranosylthymine, 2,2′-Anhydro-11-beta-D-arabinofuranosylthymine, 2.2′-Anhydro-5-methyluridine, CHEMBL3251296, SCHEMBL13497182, WLLOAUCNUMYOQI-JAGXHNFQSA-, DTXSID90945097, WLLOAUCNUMYOQI-JAGXHNFQSA-N, 3-Hydroxy-2-(hydroxymethyl)-7-methyl-2,3,3a,9a-tetrahydro-6H-furo[2′,3′:4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one, AKOS015918519, CS-W008491, NA06711, AS-13988, F12166, EN300-6732134, (2R,3R,3aS,9aR)-3-hydroxy-2-(hydroxymethyl)-7-methyl-2,3,3a,9a-tetrahydrofuro[[?]:[?]]oxazolo[[?]]pyrimidin-6-one, (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.0,dodeca-8,11-dien-10-one, 2,2′-Anhydro-5-methyl-D-uridine;2,2′-Anhydro-(1-b-D-arabinofuranosyl)-5-methyluracil;2,2′-Anhydro-D-thymidine, 6H-Furo(2′,3′:4,5)oxazolo(3,2-a)pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R-(2alpha,3beta,3abeta,9abeta))-, InChI=1/C10H12N2O5/c1-4-2-12-9-7(6(14)5(3-13)16-9)17-10(12)11-8(4)15/h2,5-7,9,13-14H,3H2,1H3/t5-,6-,7+,9-/m1/s1

This compound serves as a key intermediate in the synthesis of modified nucleosides for antiviral and anticancer research. It is particularly useful in studying RNA metabolism and enzyme inhibition mechanisms. Researchers also employ it in the development of prodrugs targeting viral polymerases. Its rigid tricyclic structure makes it a valuable scaffold for probing nucleic acid interactions.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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