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

• ChemBase ID: 155182
• Molecular Formular: C15H19NO9S
• Molecular Mass: 389.37766
• Monoisotopic Mass: 389.07805219
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: S=C=N[C@@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C15H19NO9S/c1-7(17)21-5-11-12(22-8(2)18)13(23-9(3)19)14(24-10(4)20)15(25-11)16-6-26/h11-15H,5H2,1-4H3/t11-,12-,13+,14-,15-/m1/s1
• InChIKey: WOWNQYXIQWQJRJ-UXXRCYHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-isothiocyanatooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-isothiocyanatooxan-2-yl]methyl acetate
• Synonyms: GITC; 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

Database IDs

• CAS Number: 14152-97-7
• MDL Number: MFCD00043085
• Beilstein Number: 56699
• PubChem SID: 162249320; 24900314
• PubChem CID: 99462

CALCULATED PROPERTIES

• Acid pKa: 15.050603
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.42018956
• LogD (pH = 7.4): 0.42018953
• Log P: 0.42018956
• Molar Refractivity: 85.5972 cm^3
• Polarizability: 35.540157 Å^3
• Polar Surface Area: 126.79 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 114-116 °C(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: for HPLC derivatization
• Empirical Formula (Hill Notation): C15H19NO9S

DETAILS

Sigma Aldrich - T5783

Application
Chiral reagent for resolution of amino acid derivatives.
Packaging
1 g in glass bottle
100 mg in glass bottle