(2S)-1-[(2R,3R)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate

• ChemBase ID: 175922
• Molecular Formular: C29H53NO5
• Molecular Mass: 495.73482
• Monoisotopic Mass: 495.3923738
• SMILES: C1(=O)[C@@H]([C@H](O1)C[C@@H](OC(=O)[C@H](CC(C)C)NC=O)CCCCCCCCCCC)CCCCCC
• Canonical SMILES: CCCCCCCCCCC[C@@H](C[C@H]1OC(=O)[C@@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
• InChI: InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25+,26-,27+/m0/s1
• InChIKey: AHLBNYSZXLDEJQ-YYGZZXRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R,3R)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
• IUPAC Traditional name: (2S)-1-[(2R,3R)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
• Synonyms: [2R-[2α(S*),3β]]-N-Formyl-L-leucine 1-[(3-Hexyl-4-oxo-2-oxetanyl)methyl]dodecyl Ester; (S,S,R,R)-Orlistat

Database IDs

• CAS Number: 111466-62-7
• PubChem SID: 164231832
• PubChem CID: 11145466

CALCULATED PROPERTIES

• Acid pKa: 12.743767
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 8.106578
• LogD (pH = 7.4): 8.106576
• Log P: 8.106578
• Molar Refractivity: 139.9443 cm^3
• Polarizability: 56.149376 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O686490

Orlistat isomer. Used in the asymmetric synthesis of Orlistat (O686500).

REFERENCES

• Barbier, P., et al.: Helv. Chimica Acta, 70, 196 (1987)