[(2R,3R,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-isothiocyanatooxan-2-yl]methyl benzoate

• ChemBase ID: 137256
• Molecular Formular: C35H27NO9S
• Molecular Mass: 637.65518
• Monoisotopic Mass: 637.14065245
• SMILES: c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: S=C=N[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@H]([C@@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• InChI: InChI=1S/C35H27NO9S/c37-32(23-13-5-1-6-14-23)41-21-27-28(43-33(38)24-15-7-2-8-16-24)29(44-34(39)25-17-9-3-10-18-25)30(31(42-27)36-22-46)45-35(40)26-19-11-4-12-20-26/h1-20,27-31H,21H2/t27-,28-,29+,30-,31-/m1/s1
• InChIKey: RITGYQZMPNVVEG-PXPWAULYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-isothiocyanatooxan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-isothiocyanatooxan-2-yl]methyl benzoate
• Synonyms: BGITC; 2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl isothiocyanate; 2,3,4,6-四-O-苯甲酰基-β-D-吡喃葡萄糖基异硫氰酸酯

Database IDs

• CAS Number: 132413-50-4
• MDL Number: MFCD00075064
• Beilstein Number: 6692862
• PubChem SID: 162231521; 24860334
• PubChem CID: 11966661

CALCULATED PROPERTIES

• Acid pKa: 15.040106
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 8.636888
• LogD (pH = 7.4): 8.636888
• Log P: 8.636888
• Molar Refractivity: 168.2792 cm^3
• Polarizability: 66.17989 Å^3
• Polar Surface Area: 126.79 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 150-152 °C(lit.)
• Optical Rotation: [α]20/D +29±1°, c = 1% in chloroform stab. with amylenes; [α]25/D +29°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39
• 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: ≥98.0% (HPLC); 99%
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C35H27NO9S

DETAILS

Sigma Aldrich - 86729

Other Notes
Chiral derivatizing reagent for the determination of enantiomeric purity of amino acids amines, amino alcohols and epoxides (after conversion to an amino alcohol with an amine).; Thiourea derivatives are assayed in higher sensitivity than the corresponding acetyl deriv.1