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CAS 37776-25-3

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2,3,5-tri-O-benzyl-D-arabinofuranose

Description:
2,3,5-Tri-O-benzyl-D-arabinofuranose is a carbohydrate derivative characterized by the presence of three benzyl groups attached to the hydroxyl positions at the 2, 3, and 5 positions of the D-arabinofuranose sugar. This compound is a furanose form of D-arabinose, which is a five-membered ring structure. The introduction of benzyl groups enhances the lipophilicity and stability of the molecule, making it useful in various synthetic applications, particularly in organic synthesis and carbohydrate chemistry. It is typically a white to off-white crystalline solid, soluble in organic solvents such as dichloromethane and methanol, but less soluble in water due to the bulky benzyl substituents. The compound can be utilized as a glycosyl donor in glycosylation reactions, facilitating the formation of glycosidic bonds in the synthesis of oligosaccharides and glycosides. Additionally, its structural features make it a valuable intermediate in the development of pharmaceuticals and other bioactive compounds.
Formula:C26H28O5
InChI:InChI=1/C26H28O5/c27-26-25(30-18-22-14-8-3-9-15-22)24(29-17-21-12-6-2-7-13-21)23(31-26)19-28-16-20-10-4-1-5-11-20/h1-15,23-27H,16-19H2/t23-,24-,25+,26?/m1/s1
Synonyms:
  • 2,3,5-tri-O-benzylarabinofuranose
  • D-arabinofuranose, 2,3,5-tris-O-(phenylmethyl)-
  • 2,3,5-TRI-O-BENZYL-D-ARABINOFURANOSE
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