methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(4-nitrophenoxycarbonyl)oxy]oxane-2-carboxylate

• ChemBase ID: 169661
• Molecular Formular: C20H21NO14
• Molecular Mass: 499.37904
• Monoisotopic Mass: 499.09620436
• SMILES: O(c1ccc(cc1)[N+](=O)[O-])C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C20H21NO14/c1-9(22)30-14-15(31-10(2)23)17(32-11(3)24)19(34-16(14)18(25)29-4)35-20(26)33-13-7-5-12(6-8-13)21(27)28/h5-8,14-17,19H,1-4H3/t14-,15-,16-,17+,19-/m0/s1
• InChIKey: UOZDLZHZVWFBBG-CWLGOENISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(4-nitrophenoxycarbonyl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(4-nitrophenoxycarbonyl)oxy]oxane-2-carboxylate
• Synonyms: [Methyl(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate]-4-nitro-phenyl Carbonate; β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate)

Database IDs

• PubChem SID: 162263793
• PubChem CID: 10696682

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 1.5153648
• LogD (pH = 7.4): 1.5153648
• Log P: 1.5153648
• Molar Refractivity: 105.8918 cm^3
• Polarizability: 43.017246 Å^3
• Polar Surface Area: 195.78 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - G450200

Intermediate used in the addition of protected Glucopyranuronic Acid.