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

• ChemBase ID: 104038
• 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-RGDJUOJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• Synonyms: Acetobromo-α-D-glucose; Acetobromoglucose; Bromo 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside; Acetobromo glucose; BROMO-2,3,4,6-TETRA-O-ACETYL-α-D-GLUCOPYRANOSE; 1-Bromo-α-D-glucose tetraacetate; 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide; Acetobromo-α-D-glucose

Database IDs

• CAS Number: 572-09-8
• EC Number: 209-339-0
• MDL Number: MFCD00063254
• Beilstein Number: 96669
• PubChem SID: 24845061; 162092730; 24890582
• PubChem CID: 101776

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: Acetone; Chloroform; Dichloromethane; Ethanol; Ether; Ethyl; Methanol,THF
• Apperance: White too Off-White Solid
• Melting Point: 86-87°C; 86-89 °C
• Optical Rotation: [α]20/D +195±10°, c = 3% in chloroform

Safety Information

• Storage Condition: 0°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: nwg
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; ≥95% (TLC); ≥95.0% (AT)
• Grade: purum
• Contains: ~1% CaCO3 as stabilizer; 1% CaCO3 as stabilizer
• Quality Level: PREMIUM
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C14H19BrO9

DETAILS

MP Biomedicals - 02154219

(Acetobromo glucose) Purity: ≥98%

Sigma Aldrich - A1750

Application
Acetobromo-α-D-glucose is used as a possible poly (ethylene terephthalate) (PET) surface modification reagent to increase its blood compatibility.

Sigma Aldrich - 00530

Other Notes
Glucose derivative used for the β-glucosylation of alcohols (Königs-Knorr synthesis) in the presence of an activator, e.g. metal salts 1,2,3; Radical substitution at C-14
Application
Acetobromo-α-D-glucose is used as a possible poly (ethylene terephthalate) (PET) surface modification reagent to increase its blood compatibility.