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

• ChemBase ID: 151042
• Molecular Formular: C40H50O7Si2
• Molecular Mass: 698.9918
• Monoisotopic Mass: 698.309507
• SMILES: CC(=O)O[C@H]([C@@H](CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)O)[C@@H]([C@H](C=O)O)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)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)O[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)O
• InChI: InChI=1S/C40H50O7Si2/c1-30(42)46-37(36(44)29-45-48(39(2,3)4,31-20-12-8-13-21-31)32-22-14-9-15-23-32)38(35(43)28-41)47-49(40(5,6)7,33-24-16-10-17-25-33)34-26-18-11-19-27-34/h8-28,35-38,43-44H,29H2,1-7H3/t35-,36+,37+,38+/m0/s1
• InChIKey: TVXPYOJFXNMPNJ-ZPAWJIGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-1,4-bis[(tert-butyldiphenylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4R,5R)-1,4-bis[(tert-butyldiphenylsilyl)oxy]-2,5-dihydroxy-6-oxohexan-3-yl acetate
• Synonyms: 4-O-Acetyl-3,6-di-O-(tert-butyldiphenylsilyl)-D-glucal; 4-O-乙酰基-3,6-二-O-(叔丁基二苯基甲硅烷基)-D-葡萄烯糖

Database IDs

• CAS Number: 308103-44-8
• MDL Number: MFCD01321281
• PubChem SID: 24870829; 162245201
• PubChem CID: 71311497

CALCULATED PROPERTIES

• Acid pKa: 11.787605
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 8.4595995
• LogD (pH = 7.4): 8.459582
• Log P: 8.4596
• Molar Refractivity: 184.9701 cm^3
• Polarizability: 77.89617 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]25/D +7°, c = 1.5 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Impurities: 3-5% ethyl acetate to induce mobility
• Empirical Formula (Hill Notation): C40H48O5Si2

DETAILS

Sigma Aldrich - 472816

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1
Packaging
100, 500 mg in glass bottle