(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (2R,5S)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

• ChemBase ID: 172656
• Molecular Formular: C16H26O5S
• Molecular Mass: 330.43964
• Monoisotopic Mass: 330.15009493
• SMILES: S1C[C@H](O[C@H]1C(=O)O[C@@H]1C[C@@H](CC[C@H]1C(C)C)C)OC(=O)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@H]1SC[C@H](O1)OC(=O)C)C(C)C
• InChI: InChI=1S/C16H26O5S/c1-9(2)12-6-5-10(3)7-13(12)20-15(18)16-21-14(8-22-16)19-11(4)17/h9-10,12-14,16H,5-8H2,1-4H3/t10-,12+,13-,14+,16-/m1/s1
• InChIKey: JYUPOLQFLIRYEQ-QPVMMRRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (2R,5S)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
• IUPAC Traditional name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
• Synonyms: (2R,5S)-5-(Acetyloxy)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester; (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

Database IDs

• CAS Number: 147126-65-6
• PubChem SID: 164228566
• PubChem CID: 29982888

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.4903495
• LogD (pH = 7.4): 3.4903495
• Log P: 3.4903495
• Molar Refractivity: 83.5526 cm^3
• Polarizability: 34.08927 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M219011

Lamivudine intermediate.

REFERENCES

• Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992)
• Jeong, L., et al.: J. Med. Chem., 36, 181 (1993).