N-(1-{[(1R,2S,3R,4S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-3-{[(1S,2S,3R,4S,5S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}propan-2-yl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide

• ChemBase ID: 161087
• Molecular Formular: C24H28F3N3O11
• Molecular Mass: 591.4878296
• Monoisotopic Mass: 591.16759339
• SMILES: c1cc(ccc1C(=O)NC(CO[C@H]1[C@@H]([C@@H](C2O[C@@H]1CO2)O)O)CO[C@@H]1[C@H]2O[C@H]([C@H]([C@@H]1O)O)OC2)C1(N=N1)C(F)(F)F
• Canonical SMILES: O[C@@H]1[C@H](OCC(NC(=O)c2ccc(cc2)C2(N=N2)C(F)(F)F)CO[C@@H]2[C@H]3COC(O3)[C@H]([C@H]2O)O)[C@@H]2CO[C@@H]([C@H]1O)O2
• InChI: InChI=1S/C24H28F3N3O11/c25-24(26,27)23(29-30-23)10-3-1-9(2-4-10)20(35)28-11(5-36-18-12-7-38-21(40-12)16(33)14(18)31)6-37-19-13-8-39-22(41-13)17(34)15(19)32/h1-4,11-19,21-22,31-34H,5-8H2,(H,28,35)/t11?,12-,13+,14-,15-,16+,17+,18-,19-,21?,22+/m1/s1
• InChIKey: MGQHSAUOWYOJDD-HWKXEUMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(1-{[(1R,2S,3R,4S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-3-{[(1S,2S,3R,4S,5S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}propan-2-yl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide
• IUPAC Traditional name: N-(1-{[(1R,2S,3R,4S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-3-{[(1S,2S,3R,4S,5S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}propan-2-yl)-4-[3-(trifluoromethyl)diazirin-3-yl]benzamide
• Synonyms: 4,4'-O-[2-[[4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzoyl]amino]-1,3-propanediyl]bis-1,4-anhydro-D-mannose; 2-N-[4-(1-Azitrifluoroethyl)benzoyl]-1,3-bis-(1,6-anhydro-D-mannos -4-yloxy)-2-propylamine

Database IDs

• PubChem SID: 162255222
• PubChem CID: 71313609

CALCULATED PROPERTIES

• Acid pKa: 11.9757595
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.2007122
• LogD (pH = 7.4): -0.20072338
• Log P: -0.20071186
• Molar Refractivity: 123.7686 cm^3
• Polarizability: 49.135967 Å^3
• Polar Surface Area: 190.12 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water

DETAILS

Toronto Research Chemicals - A927505

Intermediate in the production of ATB-BMPA.