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

• ChemBase ID: 172583
• Molecular Formular: C14H24O4S
• Molecular Mass: 288.40296
• Monoisotopic Mass: 288.13953025
• SMILES: O[C@H]1CS[C@@H](O1)C(=O)O[C@@H]1C[C@@H](CC[C@H]1C(C)C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@H]1SC[C@@H](O1)O)C(C)C
• InChI: InChI=1S/C14H24O4S/c1-8(2)10-5-4-9(3)6-11(10)17-13(16)14-18-12(15)7-19-14/h8-12,14-15H,4-7H2,1-3H3/t9-,10+,11-,12-,14-/m1/s1
• InChIKey: KXKDZLRTIFHOHW-CYRBOEJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate
• IUPAC Traditional name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate
• Synonyms: (2R,5R)-5-Hydroxy[1,3]oxathiolane-2-carboxylic Acid L-Menthol Ester,(1R,2S,5R)-Menthol-5R-hydroxy Acid 2-Isopropyl-5-methyl-cyclohexyl Ester; HME; (1R,2S,5R)-Menthol-5R-hydroxy-[1,3]-oxathiolane-2R-carboxylate

Database IDs

• CAS Number: 147126-62-3
• PubChem SID: 164228493
• PubChem CID: 15383325

CALCULATED PROPERTIES

• Acid pKa: 12.049318
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.0492241
• LogD (pH = 7.4): 3.0492146
• Log P: 3.0492241
• Molar Refractivity: 74.4011 cm^3
• Polarizability: 30.24091 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White To Off-White Solid
• Melting Point: 99-101°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M219050

Lamivudine (L172500) intermediate.

REFERENCES

• Schinazi, R., et al.: Antimicrob. Agents Chemother., 36, 672 (1992)
• Siddiqui, M.A., et al.: Chirality, 6, 156 (1992)