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CAS 160549-10-0

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

Description:
2,3,5-Tri-O-benzyl-D-arabinofuranose is a synthetic 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 typically used in organic synthesis and carbohydrate chemistry due to its ability to serve as a glycosyl donor or acceptor in various reactions. The benzyl groups enhance the lipophilicity and stability of the molecule, making it more suitable for certain chemical transformations. The furanose form indicates that the sugar adopts a five-membered ring structure, which is common in many biologically relevant carbohydrates. Its molecular structure contributes to its reactivity and potential applications in the synthesis of glycosides and other complex carbohydrates. Additionally, the compound's properties, such as solubility and reactivity, can be influenced by the presence of the benzyl groups, making it a valuable intermediate in the development of glycosylated compounds in medicinal chemistry and biochemistry.
Formula:C26H28O5
InChI:InChI=1S/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
InChI key:NAQUAXSCBJPECG-DYXQDRAXSA-N
SMILES:C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H](C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Synonyms:
  • (3S,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol
  • D-Arabinofuranose, 2,3,5-tris-O-(phenylmethyl)-
  • 2,3,5-Tris-O-(phenylmethyl)-D-arabinofuranose
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