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

• ChemBase ID: 151094
• Molecular Formular: C16H30O8Si
• Molecular Mass: 378.4901
• Monoisotopic Mass: 378.17099445
• SMILES: CC(=O)O[C@H]([C@@H](CO[Si](C)(C)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)(C)C)O)OC(=O)C)OC(=O)C)O
• InChI: InChI=1S/C16H30O8Si/c1-10(18)23-14(12(20)8-17)15(24-11(2)19)13(21)9-22-25(6,7)16(3,4)5/h8,12-15,20-21H,9H2,1-7H3/t12-,13+,14+,15+/m0/s1
• InChIKey: DGPMSALVNCCUAW-GBJTYRQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-4-(acetyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4R,5R)-4-(acetyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• Synonyms: 3,4-Di-O-acetyl-6-O-(tert-butyldimethylsilyl)-D-glucal; 3,4-二-O-乙酰基-6-O-(-叔丁甲基甲硅烷)-D-葡萄醛

Database IDs

• CAS Number: 117136-33-1
• MDL Number: MFCD01321277
• PubChem SID: 24870825; 162245252
• PubChem CID: 71311501

CALCULATED PROPERTIES

• Acid pKa: 11.564326
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.27920038
• LogD (pH = 7.4): -0.27922973
• Log P: -0.2792
• Molar Refractivity: 85.4967 cm^3
• Polarizability: 36.84274 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: >113 °C; >235.4 °F
• Density: 1.044 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Optical Rotation: [α]20/D -7°, c = 1.4 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C16H28O6Si

DETAILS

Sigma Aldrich - 472778

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1
Packaging
100 mg in glass bottle