(2R,3R,4S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-{[(2R,3R,4R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy}oxane-3,4,5-triol

• ChemBase ID: 138792
• Molecular Formular: C44H56O9Si2
• Molecular Mass: 785.08104
• Monoisotopic Mass: 784.34628644
• SMILES: CC(C)(C)[Si](c1ccccc1)(c1ccccc1)OC[C@@H]1[C@@H]([C@@H]([C@H](C(O1)O[C@@H]1[C@@H](C=CO[C@@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](O)C(O[C@H]2[C@H](OC=C[C@H]2O)CO[Si](C(C)(C)C)(c2ccccc2)c2ccccc2)O[C@@H]([C@@H]1O)CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C44H56O9Si2/c1-43(2,3)54(31-19-11-7-12-20-31,32-21-13-8-14-22-32)50-29-36-38(46)39(47)40(48)42(52-36)53-41-35(45)27-28-49-37(41)30-51-55(44(4,5)6,33-23-15-9-16-24-33)34-25-17-10-18-26-34/h7-28,35-42,45-48H,29-30H2,1-6H3/t35-,36-,37-,38+,39+,40-,41-,42?/m1/s1
• InChIKey: AFFPFDIIVCVTRH-MEZNOVCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-{[(2R,3R,4R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-{[(2R,3R,4R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy}oxane-3,4,5-triol
• Synonyms: 6,6′-Di-O-(tert-butyldiphenylsilyl)-D-lactal

Database IDs

• CAS Number: 187999-59-3
• MDL Number: MFCD01321286
• PubChem SID: 162233043; 24870835
• PubChem CID: 16213144

CALCULATED PROPERTIES

• Acid pKa: 12.196352
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 8.1166
• LogD (pH = 7.4): 8.116593
• Log P: 8.1166
• Molar Refractivity: 204.6654 cm^3
• Polarizability: 86.04326 Å^3
• Polar Surface Area: 127.07 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 85-92 °C(lit.)
• Optical Rotation: [α]20/D +10°, c = 1 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C44H56O9Si2

DETAILS

Sigma Aldrich - 472867

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