[(2R,3S,4S,5R,6R)-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]-6-isothiocyanatooxan-2-yl]methyl 2,2-dimethylpropanoate

• ChemBase ID: 146884
• Molecular Formular: C27H43NO9S
• Molecular Mass: 557.69662
• Monoisotopic Mass: 557.26585296
• SMILES: CC(C)(C)C(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Canonical SMILES: S=C=N[C@@H]1O[C@H](COC(=O)C(C)(C)C)[C@@H]([C@@H]([C@H]1OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• InChI: InChI=1S/C27H43NO9S/c1-24(2,3)20(29)33-13-15-16(35-21(30)25(4,5)6)17(36-22(31)26(7,8)9)18(19(34-15)28-14-38)37-23(32)27(10,11)12/h15-19H,13H2,1-12H3/t15-,16+,17+,18-,19-/m1/s1
• InChIKey: QCEYERYMOHEQHK-ICBNADEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6R)-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]-6-isothiocyanatooxan-2-yl]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(2R,3S,4S,5R,6R)-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]-6-isothiocyanatooxan-2-yl]methyl 2,2-dimethylpropanoate
• Synonyms: 2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl isothiocyanate; 2,3,4,6-四-O-特戊酰基-β-D-吡喃半乳糖基异硫氰酸酯

Database IDs

• CAS Number: 147948-52-5
• MDL Number: MFCD00216622
• PubChem SID: 24867343; 162241076
• PubChem CID: 16212855

CALCULATED PROPERTIES

• Acid pKa: 15.049731
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 7.6183352
• LogD (pH = 7.4): 7.6183352
• Log P: 7.6183352
• Molar Refractivity: 140.4068 cm^3
• Polarizability: 57.44468 Å^3
• Polar Surface Area: 126.79 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 142-145 °C(lit.)
• Optical Rotation: [α]20/D +6.5±0.5°, 1 hr, c = 1% in chloroform stab. with amylenes; [α]20/D +6.5°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (sum of enantiomers, HPLC); ≥98%
• Grade: Flukabrand™ ChiraSelect reagent; for chiral derivatization
• Optical Purity: ee: ≥99% (HPLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C27H43NO9S

DETAILS

Sigma Aldrich - 437050

Packaging
100 mg in glass bottle
Legal Information
Flukabrand is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 88102

Other Notes
Derivatizing agent for amino acids and other compounds carrying amino groups to determine their enantiomeric purity1