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

• ChemBase ID: 138852
• Molecular Formular: C24H48O9Si2
• Molecular Mass: 536.80352
• Monoisotopic Mass: 536.28368618
• SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H](C=CO[C@@H]1CO[Si](C)(C)C(C)(C)C)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@H](OC=C[C@H]2O)CO[Si](C(C)(C)C)(C)C)O[C@@H]([C@@H]1O)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C24H48O9Si2/c1-23(2,3)34(7,8)30-13-16-18(26)19(27)20(28)22(32-16)33-21-15(25)11-12-29-17(21)14-31-35(9,10)24(4,5)6/h11-12,15-22,25-28H,13-14H2,1-10H3/t15-,16-,17-,18+,19+,20-,21-,22+/m1/s1
• InChIKey: KASQKNDGTRZEQT-QPNVUBQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-6-{[(2R,3R,4R)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-6-{[(2R,3R,4R)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy}oxane-3,4,5-triol
• Synonyms: 6,6′-Di-O-(tert-butyldimethylsilyl)-D-lactal; 6,6′-二-O-(叔丁基二甲基甲硅烷基)-D-醛糖内酯

Database IDs

• CAS Number: 142800-37-1
• PubChem SID: 162233103; 24870834
• PubChem CID: 51063110

CALCULATED PROPERTIES

• Acid pKa: 12.196358
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.8122
• LogD (pH = 7.4): 1.812193
• Log P: 1.8122
• Molar Refractivity: 125.8886 cm^3
• Polarizability: 55.153522 Å^3
• Polar Surface Area: 127.07 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 56-62 °C(lit.)
• Optical Rotation: [α]20/D +16.0°, c = 1.1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C24H48O9Si2

DETAILS

Sigma Aldrich - 472859

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