(4S,5S,6S)-6-[(1R)-2-[(tert-butyldiphenylsilyl)oxy]-1-hydroxyethyl]-5-hydroxy-2-oxo-1,3-dioxane-4-carbaldehyde

• ChemBase ID: 151417
• Molecular Formular: C23H28O7Si
• Molecular Mass: 444.54972
• Monoisotopic Mass: 444.16042977
• SMILES: CC(C)(C)[Si](c1ccccc1)(c1ccccc1)OC[C@H]([C@H]1[C@@H]([C@H](OC(=O)O1)C=O)O)O
• Canonical SMILES: O=C[C@H]1OC(=O)O[C@H]([C@@H]1O)[C@@H](CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)O
• InChI: InChI=1S/C23H28O7Si/c1-23(2,3)31(16-10-6-4-7-11-16,17-12-8-5-9-13-17)28-15-18(25)21-20(26)19(14-24)29-22(27)30-21/h4-14,18-21,25-26H,15H2,1-3H3/t18-,19-,20-,21+/m1/s1
• InChIKey: OXQFQHKHZPNZSN-NCYKPQTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S,6S)-6-[(1R)-2-[(tert-butyldiphenylsilyl)oxy]-1-hydroxyethyl]-5-hydroxy-2-oxo-1,3-dioxane-4-carbaldehyde
• IUPAC Traditional name: (4S,5S,6S)-6-[(1R)-2-[(tert-butyldiphenylsilyl)oxy]-1-hydroxyethyl]-5-hydroxy-2-oxo-1,3-dioxane-4-carbaldehyde
• Synonyms: 6-O-(tert-Butyldiphenylsilyl)-D-galactal cyclic carbonate; 6-O-(叔丁基二苯基甲硅烷基)-D-半乳醛环碳酸酯

Database IDs

• CAS Number: 151265-18-8
• MDL Number: MFCD01321370
• PubChem SID: 162245571; 24871706
• PubChem CID: 71311515

CALCULATED PROPERTIES

• Acid pKa: 10.750484
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.6344976
• LogD (pH = 7.4): 3.6343064
• Log P: 3.6345
• Molar Refractivity: 109.0959 cm^3
• Polarizability: 45.883587 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -3 °C(lit.)
• Optical Rotation: [α]20/D -40.0°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: 97%
• Contains: 5% ethyl acetate as mobility inducer
• Empirical Formula (Hill Notation): C23H26O5Si

DETAILS

Sigma Aldrich - 480681

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