(3S,9aR)-3-(propan-2-yl)-hexahydro-2H-[1,3]oxazolo[3,2-d][1,4]thiazepin-5-one

• ChemBase ID: 141383
• Molecular Formular: C10H17NO2S
• Molecular Mass: 215.31248
• Monoisotopic Mass: 215.09799979
• SMILES: CC(C)[C@H]1CO[C@H]2N1C(=O)CSCC2
• Canonical SMILES: CC([C@H]1CO[C@H]2N1C(=O)CSCC2)C
• InChI: InChI=1S/C10H17NO2S/c1-7(2)8-5-13-10-3-4-14-6-9(12)11(8)10/h7-8,10H,3-6H2,1-2H3/t8-,10-/m1/s1
• InChIKey: DCIDQFQEFRCDOM-PSASIEDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,9aR)-3-(propan-2-yl)-hexahydro-2H-[1,3]oxazolo[3,2-d][1,4]thiazepin-5-one
• IUPAC Traditional name: (3S,9aR)-3-isopropyl-hexahydro-[1,3]oxazolo[3,2-d][1,4]thiazepin-5-one
• Synonyms: Gleason chiral auxiliary; (7R,10S)-(+)-1-Aza-10-isopropyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone; Gleason 手性助剂; (7R,10S)-(+)-1-氮杂-10-异丙基-8-氧杂-4-硫杂双环[5.3.0]-2-癸酮

Database IDs

• MDL Number: MFCD08276884
• PubChem SID: 24884924; 162235617
• PubChem CID: 11514032

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4370865
• LogD (pH = 7.4): 1.4370865
• Log P: 1.4370865
• Molar Refractivity: 56.498 cm^3
• Polarizability: 22.672434 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 142-146 °C

Safety Information

• German water hazard class: 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C10H17NO2S

DETAILS

Sigma Aldrich - 667587

Application
This chiral lactam auxiliary has been successfully employed in the stereocontrolled synthesis of all carbon quaternary centers. The unique methodology developed by Gleason allows for the creation of either antipode of the product using a single isomer of the auxiliary.1
Gleason Chiral Auxiliary
Packaging
1 g in glass bottle