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CAS 89025-46-7

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2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride

Description:
2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl fluoride is a glycosyl fluoride derivative of glucose, characterized by the presence of four benzyl groups attached to the hydroxyl positions of the glucopyranose ring. This compound is typically used in organic synthesis, particularly in glycosylation reactions, due to the reactivity of the fluoride group, which can act as a good leaving group. The benzyl groups enhance the lipophilicity and stability of the molecule, making it more soluble in organic solvents. The alpha configuration indicates that the anomeric hydroxyl group is in the axial position, which influences the compound's reactivity and stereochemistry in subsequent reactions. Additionally, this compound is of interest in carbohydrate chemistry and can serve as a building block for more complex glycosides or oligosaccharides. Its synthesis and manipulation require careful handling due to the potential reactivity of the fluoride moiety and the presence of multiple aromatic groups, which can affect the compound's physical properties, such as melting point and solubility.
Formula:C34H35FO5
InChI:InChI=1/C34H35FO5/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-34H,21-25H2/t30-,31-,32+,33-,34+/m1/s1
Synonyms:
  • 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl fluoride
  • 89025-46-7
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