(2R,3R,4R,5R)-4-(acetyloxy)-1-[(tert-butyldiphenylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate

• ChemBase ID: 138734
• Molecular Formular: C26H34O8Si
• Molecular Mass: 502.62886
• Monoisotopic Mass: 502.20229458
• SMILES: CC(=O)O[C@H]([C@@H](CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)O)[C@@H]([C@H](C=O)O)OC(=O)C
• Canonical SMILES: O=C[C@@H]([C@H]([C@@H]([C@@H](CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)O)OC(=O)C)OC(=O)C)O
• InChI: InChI=1S/C26H34O8Si/c1-18(28)33-24(22(30)16-27)25(34-19(2)29)23(31)17-32-35(26(3,4)5,20-12-8-6-9-13-20)21-14-10-7-11-15-21/h6-16,22-25,30-31H,17H2,1-5H3/t22-,23+,24+,25+/m0/s1
• InChIKey: PYGIMOKQSQTVMY-ZYQDXHPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-4-(acetyloxy)-1-[(tert-butyldiphenylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4R,5R)-4-(acetyloxy)-1-[(tert-butyldiphenylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• Synonyms: 3,4-Di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-D-glucal

Database IDs

• CAS Number: 151797-32-9
• MDL Number: MFCD01321279
• PubChem SID: 162232985; 24870827
• PubChem CID: 71310175

CALCULATED PROPERTIES

• Acid pKa: 11.564294
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.8729997
• LogD (pH = 7.4): 2.8729703
• Log P: 2.873
• Molar Refractivity: 124.8851 cm^3
• Polarizability: 52.21286 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: >113 °C; >235.4 °F
• Refractive Index: n20/D 1.456(lit.)
• Optical Rotation: [α]20/D +9°, c = 1.1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C26H32O6Si

DETAILS

Sigma Aldrich - 472794

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