[(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate

• ChemBase ID: 92225
• Molecular Formular: C14H19BrO9
• Molecular Mass: 411.19926
• Monoisotopic Mass: 410.02124419
• SMILES: Br[C@H]1O[C@@H]([C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H](Br)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14+/m1/s1
• InChIKey: CYAYKKUWALRRPA-HTOAHKCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• Synonyms: 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl bromide; Acetobromo-α-D-galactose; 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl bromide; Acetobromo-α-D-Galactose; Acetobromogalactose; Bromo 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranoside; Acetobromo-a-D-galactose; Bromo-2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranose

Database IDs

• CAS Number: 3068-32-4
• MDL Number: MFCD00063686
• Beilstein Number: 96671
• PubChem SID: 162078923; 24845060; 24891250
• PubChem CID: 2734143

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.3887714
• LogD (pH = 7.4): -0.3887714
• Log P: -0.3887714
• Molar Refractivity: 78.8836 cm^3
• Polarizability: 32.837383 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Crystalline Solid
• Melting Point: 82-83°C
• Optical Rotation: [α]20/D +205±10°, c = 3% in chloroform

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (AT); ≥93% (TLC); 95+%
• Grade: technical
• Contains: ~1% CaCO3 as stabilizer; 1% CaCO3 as stabilizer
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C14H19BrO9

DETAILS

Sigma Aldrich - A7562

Application
2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl bromide is used as an organic condensation reagent for chemistries such as N- and S- galactosylation reactions and the synthesis of spacer-equipped phosphorylated di-, tri- and tetrasaccharide fragments of the O-specific polysaccharides.

Sigma Aldrich - 00525

Other Notes
Galactose derivative used for the β-galactosylation of alcohols (Königs-Knorr synthesis)1,2; Preparation of tri-O-acetylgalactal3

Toronto Research Chemicals - B687000

Temperature and moisture sensitive; Store in freezer; Stabilized with 2% CaCO3