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CAS 572-09-8

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α-Acetobromoglucose

Description:
α-Acetobromoglucose, with the CAS number 572-09-8, is a halogenated derivative of glucose, specifically an α-anomer of brominated glucose. This compound features a bromine atom and an acetyl group attached to the glucose structure, which influences its reactivity and solubility. It is typically a white to off-white crystalline solid, soluble in polar solvents such as water and alcohols, due to the presence of hydroxyl groups. The acetyl group enhances its lipophilicity, making it more versatile in organic synthesis. α-Acetobromoglucose is often used as a reagent in organic chemistry, particularly in glycosylation reactions, where it serves as a glycosyl donor. Its bromine atom can participate in nucleophilic substitution reactions, making it valuable in the synthesis of various glycosides and other carbohydrate derivatives. Additionally, the compound's stereochemistry plays a crucial role in determining its biological activity and interaction with enzymes and receptors in biochemical pathways.
Formula:C14H19BrO9
InChI:InChI=1/C8H13BrO7/c1-4(12)15-6(3-11)8(16-9)7(14)5(13)2-10/h3,5-8,10,13-14H,2H2,1H3/t5-,6+,7-,8-/m1/s1
InChI key:InChIKey=CYAYKKUWALRRPA-RGDJUOJXSA-N
SMILES:O(C(C)=O)[C@H]1[C@H](OC(C)=O)[C@@H](COC(C)=O)O[C@H](Br)[C@@H]1OC(C)=O
Synonyms:
  • 1-Bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranose
  • 1-Bromo-2,3,4,6-tetra(O-acetyl)-α-<span class="text-smallcaps">D</span>-pyranoglucose
  • 1-Bromo-2,3,4,6-tetra(O-acetyl)-α-D-pyranoglucose
  • 1-Bromo-α-<span class="text-smallcaps">D</span>-glucose tetraacetate
  • 1-Bromo-α-D-glucose tetraacetate
  • 2,3,4,6-Tetra-O-acetyl-1-α-bromo-<span class="text-smallcaps">D</span>-glucopyranose
  • 2,3,4,6-Tetra-O-acetyl-1-α-bromo-D-glucopyranose
  • 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromid
  • 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
  • 2,3,4,6-Tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-bromoglucopyranose
  • See more synonyms
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