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Acetobromo-alpha-D-glucose, 97%, stab. with 2% calcium carbonate
CAS: 572-09-8 | C14H19BrO9 | 411.20 g/mol
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Catalog number L04151.09
also known as L04151-09
Price (EUR)
74,70
Each
Quantity:
10 g
Price (EUR)
74,70
Each
Chemical Identifiers
CAS572-09-8
IUPAC Name[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
Molecular FormulaC14H19BrO9
InChI KeyCYAYKKUWALRRPA-HAGGZJDPNA-N
SMILESCC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
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Specifications
Specification Sheet
Specification SheetFormpowder
Appearance (Color)White to pale cream or pale grey
Assay (Titration ex Bromide)>96.0% (corrected for stabilser)
Optical Rotation+193 ? 7? ( (c=3 in chloroform)
Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
Solubility
Soluble in ether, chloroform, ethanol, acetone, dichloromethane, ether, ethyl, methanol, and tetrahydrofuran. Insoluble in water.
Notes
Store in a cool place. Incompatible with strong oxidizing agents, acids, magnesium and aluminum.
Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
Solubility
Soluble in ether, chloroform, ethanol, acetone, dichloromethane, ether, ethyl, methanol, and tetrahydrofuran. Insoluble in water.
Notes
Store in a cool place. Incompatible with strong oxidizing agents, acids, magnesium and aluminum.
RUO – Research Use Only
General References:
- Glycosyl isothiocyanates have been prepared in good yield by heating fully O-acetylated glycosyl bromides with KSCN in the absence of solvent. With acetobromo-ɑ-D-glucose, displacement was accompanied by stereochemical inversion: Synthesis, 1228 (1995).
- Reaction with Bis(cyclopentadienyl) titanium dichloride, A11456 results in 1,2-elimination providing a convenient route to the glycal: J. Org. Chem., 60, 7055 (1995).
- Forget, S. M.; Jee, A.; Smithen, D. A.; Jagdhane, R.; Anjum, S.; Beaton, S. A.; Palmer, D. R. J.; Syvitski, R. T.; Jakeman, D. L. Kinetic evaluation of glucose 1-phosphate analogues with a thymidylyltransferase using a continuous coupled enzyme assay. Org. Biomol. Chem. 2015, 13 (3), 866-875.
- Xu, Y.; Wang, W.; Cai, Y.; Yang, X.; Wang, P. G.; Zhao, W. A convenient and efficient synthesis of glycals by zinc nanoparticles. RSC Adv. 2014, 4 (87), 46662-46665.