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

• ChemBase ID: 141952
• Molecular Formular: C13H18O9
• Molecular Mass: 318.27662
• Monoisotopic Mass: 318.09508216
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H](O1)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12+,13+/m1/s1
• InChIKey: IHNHAHWGVLXCCI-NDBYEHHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• Synonyms: NSC 108078; 1,2,3,5-Tetra-O-acetyl-α-D-arabinofuranose; 1,2,3,5-四-O-乙酰基-α-D-阿拉伯呋喃糖

Database IDs

• CAS Number: 43225-70-3
• MDL Number: MFCD05865195
• PubChem SID: 162236184; 24882691
• PubChem CID: 11088423

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.5377026
• LogD (pH = 7.4): -0.5377026
• Log P: -0.5377026
• Molar Refractivity: 66.5669 cm^3
• Polarizability: 28.05088 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 140 °C/0.01 mmHg(lit.)
• Density: 1.31 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4500(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥80%
• Grade: technical grade
• Empirical Formula (Hill Notation): C13H18O9

DETAILS

Sigma Aldrich - 634808

Packaging
5 g in glass bottle
Application
Reactant for:
• Asymmetric synthesis of hydroxyl acetylpentofuranosides via diastereoselective enzymic deacetylation through Candida antarctica B lipase (CAL B)-catalyzed alcoholysis1
• Reaction with trimethylaluminum in synthesis of 1,2-O-isopropylidene D-ribofuranose2
• Synthesis of oligosaccharides of motifs D and E of arabinogalactan present in Mycobacterium tuberculosis via coupling and glycosylation reactions3