(1R,9R,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one

• ChemBase ID: 133884
• Molecular Formular: C10H12N2O4
• Molecular Mass: 224.21328
• Monoisotopic Mass: 224.07970687
• SMILES: Cc1cn2c(nc1=O)O[C@H]1C[C@@H]2O[C@@H]1CO
• Canonical SMILES: OC[C@H]1O[C@H]2C[C@@H]1Oc1n2cc(c(=O)n1)C
• InChI: InChI=1S/C10H12N2O4/c1-5-3-12-8-2-6(7(4-13)15-8)16-10(12)11-9(5)14/h3,6-8,13H,2,4H2,1H3/t6-,7-,8-/m1/s1
• InChIKey: JCSNHEYOIASGKU-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.0^2,^7]dodeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,9R,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.0^2,^7]dodeca-3,6-dien-5-one
• Synonyms: 2,3′-Anhydrothymidine

Database IDs

• CAS Number: 15981-92-7
• PubChem SID: 162228161
• PubChem CID: 457982

CALCULATED PROPERTIES

• Acid pKa: 14.588505
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.029251672
• LogD (pH = 7.4): 0.029251644
• Log P: 0.029251672
• Molar Refractivity: 52.6216 cm^3
• Polarizability: 20.801762 Å^3
• Polar Surface Area: 71.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A4044

Application
2,3′-Anhydrothymidine may be derivitized to 5′-benzoyl-2′,3′-anhydrothymidine for use in the synthesis of 5′-Derivatives of 3′-(tetrazole-2′-yl)-3′-deoxythymidines. 2,3′-Anhydrothymidine may be contacted with thioacetic acid to produce 3′-S-acetyl-3′-thio-2′-deoxynucleosides.