(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase ID: 170635
• Molecular Formular: C11H13NO7
• Molecular Mass: 271.22342
• Monoisotopic Mass: 271.06920176
• SMILES: [C@H]1(OC(=O)ON2C(=O)CCC2=O)CO[C@@H]2[C@H]1CCO2
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)O[C@H]1CO[C@@H]2[C@H]1CCO2
• InChI: InChI=1S/C11H13NO7/c13-8-1-2-9(14)12(8)19-11(15)18-7-5-17-10-6(7)3-4-16-10/h6-7,10H,1-5H2/t6-,7-,10+/m0/s1
• InChIKey: VCFNCYVHQSHFRH-MHYGZLNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC Traditional name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 2,5-dioxopyrrolidin-1-yl carbonate
• Synonyms: Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] Ester; 1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione; [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

Database IDs

• CAS Number: 253265-97-3
• PubChem SID: 164226545
• PubChem CID: 11184820

CALCULATED PROPERTIES

• Acid pKa: 17.634138
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.056622095
• LogD (pH = 7.4): 0.056622095
• Log P: 0.056622095
• Molar Refractivity: 56.6903 cm^3
• Polarizability: 23.276972 Å^3
• Polar Surface Area: 91.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Pale-Yellow Solid

DETAILS

Toronto Research Chemicals - H942810

Darunavir intermediate.

REFERENCES

• Ghosh, A., et al.: J. Med. Chem., 39, 3278 (1996)
• Ghosh, A., et al.: Bioorg. Med. Chem. Lett., 1998, 8, 687 (1996)
• Richman, D., et al.: Nature, 410, 995 (1996)
• Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (1996)