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CAS 68703-51-5

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5-O-tert-Butyldimethylsilyl-2,3-O-isopropylidene-alpha,beta-D-ribofuranose

Description:
5-O-tert-Butyldimethylsilyl-2,3-O-isopropylidene-alpha,beta-D-ribofuranose is a chemical compound that belongs to the class of ribofuranosides, which are derivatives of ribose, a sugar component of RNA. This compound features a tert-butyldimethylsilyl (TBDMS) protecting group at the 5-position, which enhances its stability and solubility in organic solvents, making it useful in synthetic organic chemistry. The 2,3-O-isopropylidene group provides additional protection for the hydroxyl groups at the 2 and 3 positions, facilitating selective reactions. The alpha and beta designations indicate the anomeric configuration of the sugar, which is crucial for its reactivity and biological activity. This compound is typically used in the synthesis of nucleosides and nucleotides, serving as an intermediate in the preparation of various biologically active molecules. Its structural complexity and protective groups make it a valuable building block in carbohydrate chemistry and medicinal chemistry applications.
Formula:C14H28O5Si
InChI:InChI=1/C14H28O5Si/c1-13(2,3)20(6,7)16-8-9-10-11(12(15)17-9)19-14(4,5)18-10/h9-12,15H,8H2,1-7H3/t9-,10-,11-,12u/m1/s1
SMILES:CC(C)(C)[Si](C)(C)OC[C@@H]1[C@@H]2[C@H](C(O)O1)OC(C)(C)O2
Synonyms:
  • 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-Ribofuranose
  • (3aR,6R,6aR)-6-[(tert-butyl-dimethyl-silyl)oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[4,3-d][1,3]dioxol-4-ol
  • 5-O-(Tert-Butyldimethylsilyl)-2,3-O-Isoproylidene-D-Ribofuranose
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