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CAS 55725-85-4

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Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside

Description:
Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside is a glycoside derivative of ribofuranose, characterized by the presence of three benzyl groups attached to the hydroxyl positions at the 2, 3, and 5 positions of the ribofuranose ring. This compound is typically used in organic synthesis and carbohydrate chemistry due to its ability to serve as a protective group for hydroxyl functionalities. The methyl group at the anomeric position enhances its stability and solubility in organic solvents. It is a white to off-white solid, and its structure contributes to its relatively low reactivity compared to unprotected ribofuranose. The presence of the benzyl groups not only provides steric hindrance but also influences the compound's solubility and reactivity, making it useful in various synthetic applications, including the synthesis of nucleosides and other carbohydrate derivatives. Additionally, it may exhibit interesting biological properties, although specific biological activity would depend on the context of its use and the presence of other functional groups in a given reaction or application.
Formula:C27H30O5
InChI:InChI=1/C27H30O5/c1-28-27-26(31-19-23-15-9-4-10-16-23)25(30-18-22-13-7-3-8-14-22)24(32-27)20-29-17-21-11-5-2-6-12-21/h2-16,24-27H,17-20H2,1H3/t24-,25-,26-,27-/m1/s1
SMILES:CO[C@H]1[C@@H]([C@@H]([C@@H](COCc2ccccc2)O1)OCc1ccccc1)OCc1ccccc1
Synonyms:
  • beta-D-ribofuranoside, methyl 2,3,5-tris-O-(phenylmethyl)-
  • Methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside
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