(4aR,7R,8R,8aR)-7-acetamido-6-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate

• ChemBase ID: 158876
• Molecular Formular: C17H21NO7
• Molecular Mass: 351.35114
• Monoisotopic Mass: 351.13180202
• SMILES: [C@@H]12[C@@H]([C@@H](C(O[C@@H]1COC(O2)c1ccccc1)O)NC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)N[C@@H]1C(O)O[C@H]2[C@@H]([C@@H]1OC(=O)C)OC(OC2)c1ccccc1
• InChI: InChI=1S/C17H21NO7/c1-9(19)18-13-15(23-10(2)20)14-12(24-16(13)21)8-22-17(25-14)11-6-4-3-5-7-11/h3-7,12-17,21H,8H2,1-2H3,(H,18,19)/t12-,13-,14+,15-,16?,17?/m1/s1
• InChIKey: OPEPHRZBCPGJGP-UUVLZXSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,7R,8R,8aR)-7-acetamido-6-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate
• IUPAC Traditional name: (4aR,7R,8R,8aR)-7-acetamido-6-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-D-galactopyranose 3-Acetate; 2-(Acetylamino)-2-deoxy-3-O-acetyl-4,6-O-benzylidene-D-galactopyranose

Database IDs

• PubChem SID: 162253011
• PubChem CID: 71312724

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 11.629295
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.3856297
• LogD (pH = 7.4): 0.38560528
• Log P: 0.38563025
• Molar Refractivity: 83.0598 cm^3
• Polarizability: 33.928173 Å^3
• Polar Surface Area: 103.32 Å^2
• Rotatable Bonds: 4

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A150835

Intermediate in the preparation of the T epitope of Threonyl