(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane-6-carboxylic acid hydrate

• ChemBase ID: 119165
• Molecular Formular: C12H20O8
• Molecular Mass: 292.2824
• Monoisotopic Mass: 292.1158176
• SMILES: [C@@]12([C@H]([C@H]3[C@@H](O1)COC(O3)(C)C)OC(O2)(C)C)C(=O)O.O
• Canonical SMILES: OC(=O)[C@]12O[C@@H]3[C@H]([C@@H]2OC(O1)(C)C)OC(OC3)(C)C.O
• InChI: InChI=1S/C12H18O7.H2O/c1-10(2)15-5-6-7(17-10)8-12(16-6,9(13)14)19-11(3,4)18-8;/h6-8H,5H2,1-4H3,(H,13,14);1H2/t6-,7+,8-,12+;/m0./s1
• InChIKey: ZFQRGFMVXLSLKZ-QCILGFJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.0^2,^6]dodecane-6-carboxylic acid hydrate
• IUPAC Traditional name: (1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.0^2,^6]dodecane-6-carboxylic acid hydrate
• Synonyms: (3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxine-8a-carboxylic acid hydrate; (-)-Diaceton-2-keto-L-gulonsäure; 2,3:4,6-Di-O-isopropyliden-α-L-xylo-2-hexulofuranosonsäure; (-)-Diacetone-2-keto-L-gulonic acid; 2,3:4,6-Di-O-isopropylidene-α-L-xylo-2-hexulofuranosonic acid; Dikegulac; (-)-2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonic acid monohydrate; 双酮古龙酸; 双酮古洛糖酸; 敌草克; (-)-2,3:4,6-二亚异丙基-2-酮-L-古洛糖酸 一水合物

Database IDs

• CAS Number: 68539-16-2
• MDL Number: MFCD00150517
• PubChem SID: 162107345; 24850824; 24858969
• PubChem CID: 16211407

CALCULATED PROPERTIES

• Acid pKa: 3.0536487
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -1.2941284
• LogD (pH = 7.4): -2.348553
• Log P: 1.1193137
• Molar Refractivity: 60.7173 cm^3
• Polarizability: 24.871696 Å^3
• Polar Surface Area: 83.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 88-90 °C(lit.); 90-94 °C
• Optical Rotation: [α]20/D -21±1°, c = 2% in methanol; [α]21/D -20°, c = 2 in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0%; 98%
• Salt Data: H2O
• Ignition Residue: ≤0.1%
• Empirical Formula (Hill Notation): C12H18O7 · H2O
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 179698

Packaging
100 g in glass bottle

Sigma Aldrich - 31462

Other Notes
Reagent for the resolution of racemic amines1,2