(2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl benzoate

• ChemBase ID: 138947
• Molecular Formular: C13H16O7
• Molecular Mass: 284.26194
• Monoisotopic Mass: 284.08960285
• SMILES: c1ccc(cc1)C(=O)OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O
• Canonical SMILES: O=C[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c1ccccc1)O)O)O)O
• InChI: InChI=1S/C13H16O7/c14-6-9(15)11(17)12(18)10(16)7-20-13(19)8-4-2-1-3-5-8/h1-6,9-12,15-18H,7H2/t9-,10+,11+,12+/m0/s1
• InChIKey: VKUVHQLMDOUYND-IRCOFANPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl benzoate
• IUPAC Traditional name: (2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl benzoate
• Synonyms: 6-O-Benzoyl-D-glucal; 6-O-苯甲酰-D-葡萄烯糖

Database IDs

• CAS Number: 58871-05-9
• MDL Number: MFCD01321275
• PubChem SID: 24870823; 162233198
• PubChem CID: 20056718

CALCULATED PROPERTIES

• Acid pKa: 11.800261
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.073061
• LogD (pH = 7.4): -1.073078
• Log P: -1.0730608
• Molar Refractivity: 67.1676 cm^3
• Polarizability: 26.667208 Å^3
• Polar Surface Area: 124.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 106-111 °C(lit.)
• Optical Rotation: [α]25/D +44°, c = 1.4 in chloroform

Safety Information

• 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): C13H14O5

DETAILS

Sigma Aldrich - 472743

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1