(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(hydroxymethyl)oxan-2-yl acetate

• ChemBase ID: 104674
• Molecular Formular: C14H20O10
• Molecular Mass: 348.3026
• Monoisotopic Mass: 348.10564684
• SMILES: O=C(O[C@@H]1O[C@@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)CO)C
• Canonical SMILES: OC[C@H]1O[C@@H](OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H20O10/c1-6(16)20-11-10(5-15)24-14(23-9(4)19)13(22-8(3)18)12(11)21-7(2)17/h10-15H,5H2,1-4H3/t10-,11-,12+,13-,14-/m1/s1
• InChIKey: FEQXFAYSNRWXDW-RKQHYHRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(hydroxymethyl)oxan-2-yl acetate; (2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-2-(hydroxymethyl)oxan-3-yl acetate
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(hydroxymethyl)oxan-2-yl acetate; (2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-2-(hydroxymethyl)oxan-3-yl acetate
• Synonyms: 1,2,3,4-Tetra-O-acetyl-β-D-glucopyranose; 1,2,3,4-TETRA-O-ACETYL-β-D-GLUCOPYRANOSE; 1,2,3,4-四-O-乙酰-β-D-吡喃葡萄糖

Database IDs

• CAS Number: 13100-46-4
• EC Number: 236-018-2
• MDL Number: MFCD00063260
• PubChem SID: 162093293; 24864350
• PubChem CID: 83136

CALCULATED PROPERTIES

• Acid pKa: 14.58155
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1680375
• LogD (pH = 7.4): -1.1680377
• Log P: -1.1680375
• Molar Refractivity: 72.5294 cm^3
• Polarizability: 30.56413 Å^3
• Polar Surface Area: 134.66 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 126-128 °C(lit.)
• Optical Rotation: [α]20/D +11°, c = 6 in chloroform

Safety Information

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

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C14H20O10

DETAILS

Sigma Aldrich - 390879

Packaging
1 g in glass bottle
Application
Phosphorylated derivatives have proven valuable in the study of substrates for inositol synthase,1 and for the preparation of anionic surfactants.2