ethyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoate

• ChemBase ID: 144862
• Molecular Formular: C11H24O3Si
• Molecular Mass: 232.39196
• Monoisotopic Mass: 232.14947116
• SMILES: CCOC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C
• Canonical SMILES: CCOC(=O)[C@@H](O[Si](C(C)(C)C)(C)C)C
• InChI: InChI=1S/C11H24O3Si/c1-8-13-10(12)9(2)14-15(6,7)11(3,4)5/h9H,8H2,1-7H3/t9-/m0/s1
• InChIKey: KOBAXFIJEBLKRZ-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoate
• IUPAC Traditional name: ethyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoate
• Synonyms: Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate; (S)-(-)-2-(叔丁基二甲基硅氧基)丙酸乙酯

Database IDs

• CAS Number: 106513-42-2
• MDL Number: MFCD00192135
• PubChem SID: 162239074; 24866603
• PubChem CID: 10966394

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.7517
• LogD (pH = 7.4): 2.7517
• Log P: 2.7517
• Molar Refractivity: 58.2056 cm^3
• Polarizability: 25.388514 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 187 °C(lit.)
• Flash Point: 175 °F; 79 °C
• Density: 0.875 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.425(lit.)
• Optical Rotation: [α]20/D -30°, c = 1.26 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: 98%
• Linear Formula: CH3CH[OSi(CH3)2C(CH3)3]CO2C2H5

DETAILS

Sigma Aldrich - 424951

Packaging
25 mL in poly bottle
Application
Precursor to the lactyl-3,4-didehydroproline didemnin B side chain.1 Starting material for the asymmetric synthesis of syn- and anti- functionalized1,2-diols.2