Date published: 2025-12-18

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Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside (CAS 4099-85-8)

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CAS Number:
4099-85-8
Molecular Weight:
204.22
Molecular Formula:
C9H16O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside, a ribofuranoside derivative, has emerged as a valuable tool in carbohydrate chemistry and nucleoside synthesis research. Its unique structure, featuring an isopropylidene group, renders it chemically versatile for various synthetic transformations. In research, this compound has been extensively utilized as a building block for the synthesis of nucleoside analogs and nucleotide mimics, owing to its ability to serve as a protected ribose moiety. Through selective deprotection strategies, researchers have employed Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside to access diverse nucleoside structures with modified sugar functionalities, enabling investigations into structure-activity relationships and biological interactions. Additionally, its role as a glycosylation precursor has been instrumental in the synthesis of oligosaccharides and glycoconjugates for studying carbohydrate-protein interactions and glycobiology. Furthermore, this compound has found applications in the synthesis of modified RNA and DNA analogs for exploring nucleic acid chemistry and nucleic acid-based technologies. Its versatility as a synthetic intermediate makes Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside a valuable asset in the arsenal of researchers aiming to manipulate carbohydrate and nucleoside structures for various scientific inquiries, from elucidating molecular recognition events to developing novel materials.


Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside (CAS 4099-85-8) References

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  2. Synthesis and anti-HBV activity of thiouracils linked via S and N-1 to the 5-position of methyl beta-D-ribofuranoside.  |  Abdel-Rahman, AA., et al. 2003. Nucleosides Nucleotides Nucleic Acids. 22: 2027-38. PMID: 14680025
  3. Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide.  |  McCartney, JL., et al. 2003. J Org Chem. 68: 10152-5. PMID: 14682713
  4. The Quaternization Reaction of 5-O-Sulfonates of Methyl 2,3-o-Isopropylidene-β-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines.  |  Dmochowska, B., et al. 2020. Molecules. 25: PMID: 32380736
  5. Characteristic 1H NMR spectra of β-d-ribofuranosides and ribonucleosides: factors driving furanose ring conformations.  |  Walczak, D., et al. 2022. RSC Adv. 12: 29223-29239. PMID: 36320749
  6. Some intramolecular rearrangements when pentofuranoses are treated with diethylaminosulphur trifluoride (DAST)  |  Lloyd, A. E., Coe, P. L., Walker, R. T., & Howarth, O. W. 1993. Journal of fluorine chemistry. 60(2-3): 239-250.
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  9. Synthesis and chromatographic study of methyl-2, 3-O-isopropylidene-5-dimethyl-arsinoyl-β-d-ribofuranoside and methyl-2, 3-O-isopropylidene-5-deoxy-5-dimethyl-thioarsinoyl-β-d-ribofuranoside  |  Gyepes, A., Schäffer, R., Bajor, G., Woller, Á., & Fodor, P. 2008. Polyhedron. 27(12): 2655-2661.
  10. N, N, N-Trimethyl-N-(methyl 5-deoxy-2, 3-O-isopropylidene-β-d-ribofuranosid-5-yl) ammonium 4-methylbenzenesulfonate sesquihydrate  |  Dmochowska, B., Sikora, K., Chojnacki, J., Wojnowski, W., & Wiśniewski, A. 2013. Acta Crystallographica Section E: Structure Reports Online. 69(7): o1019-o1020.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Methyl 2,3-O-Isopropylidene-β-D-ribofuranoside, 5 g

sc-221899
5 g
$330.00