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

• ChemBase ID: 138814
• Molecular Formular: C20H42O7Si2
• Molecular Mass: 450.71428
• Monoisotopic Mass: 450.24690675
• SMILES: CC(=O)O[C@H]([C@@H](CO[Si](C)(C)C(C)(C)C)O)[C@@H]([C@H](C=O)O)O[Si](C)(C)C(C)(C)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)O[Si](C(C)(C)C)(C)C)O
• InChI: InChI=1S/C20H42O7Si2/c1-14(22)26-17(16(24)13-25-28(8,9)19(2,3)4)18(15(23)12-21)27-29(10,11)20(5,6)7/h12,15-18,23-24H,13H2,1-11H3/t15-,16+,17+,18+/m0/s1
• InChIKey: PUTBIZQBKYLDAU-BSDSXHPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4R,5R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• Synonyms: 4-O-Acetyl-3,6-di-O-(tert-butyldimethylsilyl)-D-glucal; 4-O-乙酰基-3,6-二-O-(叔丁基二甲基甲硅烷基)-D-葡萄烯糖

Database IDs

• CAS Number: 132891-79-3
• MDL Number: MFCD01321282
• PubChem SID: 24870830; 162233065
• PubChem CID: 71310185

CALCULATED PROPERTIES

• Acid pKa: 11.797037
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.1551998
• LogD (pH = 7.4): 2.1551826
• Log P: 2.1552
• Molar Refractivity: 106.1933 cm^3
• Polarizability: 46.96684 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 324 °C(lit.)
• Flash Point: >113 °C; >235.4 °F
• Density: 0.968 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Optical Rotation: [α]20/D -19°, c = 2.1 in chloroform

Safety Information

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

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C20H40O5Si2

DETAILS

Sigma Aldrich - 472824

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