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

• ChemBase ID: 138810
• Molecular Formular: C20H20O8
• Molecular Mass: 388.368
• Monoisotopic Mass: 388.1158176
• SMILES: c1ccc(cc1)C(=O)OC[C@H]([C@H]([C@@H]([C@H](C=O)O)OC(=O)c1ccccc1)O)O
• Canonical SMILES: O=C[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c1ccccc1)O)O)OC(=O)c1ccccc1)O
• InChI: InChI=1S/C20H20O8/c21-11-15(22)18(28-20(26)14-9-5-2-6-10-14)17(24)16(23)12-27-19(25)13-7-3-1-4-8-13/h1-11,15-18,22-24H,12H2/t15-,16+,17+,18+/m0/s1
• InChIKey: FSHBWIUEGPPPIJ-BSDSXHPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-4-(benzoyloxy)-2,3,5-trihydroxy-6-oxohexyl benzoate
• IUPAC Traditional name: (2R,3R,4S,5R)-4-(benzoyloxy)-2,3,5-trihydroxy-6-oxohexyl benzoate
• Synonyms: 3,6-Di-O-benzoyl-D-glucal; 3,6-二-O-苯甲酰-D-葡萄烯糖

Database IDs

• CAS Number: 58871-06-0
• MDL Number: MFCD01321284
• PubChem SID: 162233061; 24870832
• PubChem CID: 71310184

CALCULATED PROPERTIES

• Acid pKa: 11.683092
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.4222388
• LogD (pH = 7.4): 1.4222165
• Log P: 1.4222392
• Molar Refractivity: 96.9896 cm^3
• Polarizability: 38.158024 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129-134 °C(lit.)
• Optical Rotation: [α]25/D -102°, c = 1 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: 96%
• Empirical Formula (Hill Notation): C20H18O6

DETAILS

Sigma Aldrich - 472840

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