[(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate

• ChemBase ID: 143639
• Molecular Formular: C26H43BrO9
• Molecular Mass: 579.51822
• Monoisotopic Mass: 578.20904496
• SMILES: CC(C)(C)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Canonical SMILES: Br[C@H]1O[C@H](COC(=O)C(C)(C)C)[C@H]([C@@H]([C@H]1OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• InChI: InChI=1S/C26H43BrO9/c1-23(2,3)19(28)32-13-14-15(34-20(29)24(4,5)6)16(35-21(30)25(7,8)9)17(18(27)33-14)36-22(31)26(10,11)12/h14-18H,13H2,1-12H3/t14-,15-,16+,17-,18+/m1/s1
• InChIKey: BSDBCYHGMPHOAL-SFFUCWETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• Synonyms: 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl bromide; 2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE

Database IDs

• CAS Number: 81058-27-7
• MDL Number: MFCD08275217
• Beilstein Number: 3576922
• PubChem SID: 162237857
• PubChem CID: 10886360

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 6.713411
• LogD (pH = 7.4): 6.713411
• Log P: 6.713411
• Molar Refractivity: 133.6932 cm^3
• Polarizability: 54.525154 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]/D 152.0±3.0°, c = 3 in chloroform

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (TLC); 98%
• Empirical Formula (Hill Notation): C26H43BrO9

DETAILS

Sigma Aldrich - 778621

Application
Königs-Knorr glycosyl donor with considerably lower tendency to form orthoester side products during glycosylation than the traditional acetobromoglucose1,2,3
Packaging
500 mg in glass bottle