Xylitol pentacetate
Names
IUPAC name
[(2S,4R)-2,3,4,5-tetraacetyloxypentyl] acetate
Other names
[(2S,4R)-2,3,4,5-Tetraacetyloxypentyl] acetate
D-Ribitol pentaacetate
1,2,3,4,5-penta-O-acetyl ribitol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C15H22O10/c1-8(16)21-6-13(23-10(3)18)15(25-12(5)20)14(24-11(4)19)7-22-9(2)17/h13-15H,6-7H2,1-5H3/t13-,14+,15?
    Key: NVKPIAUSOPISJK-YIONKMFJSA-N
  • CC(=O)OC[C@H](C([C@H](COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Properties
C15H22O10
Molar mass 362.331 g·mol−1
Soluble in water[1]
Solubility Soluble in methanol [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Xylitol pentacetate is an organic compound with the formula C15H22O10. It is an acetylated sugar alcohol that is used as an intermediary in the production of xylitol pentanitrate.[2] It is also commonly made to isolate and identify xylitol from complex organic mixtures.[3][1]

Synthesis

Xylitol pentacetate is made by the addition of acetic anhydride and sodium acetate to xylitol.[1]

References

  1. 1 2 3 4 Hockett, R. C.; Hudson, C. S. (1935). "Emil Fischer's Assignment of Configuration to d-Glucose. The Pentaacetates of d-Arabitol and d-Xylitol". Journal of the American Chemical Society. 57 (9): 1753. doi:10.1021/ja01312a502. ISSN 0002-7863.
  2. ↑ Wright, I. G.; Hayward, L. D. (February 1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.
  3. ↑ Moers, M.E.C.; Jones, D.M.; Eakin, P.A.; Fallick, A.E.; Griffiths, H.; Larter, S.R. (1993). "Carbohydrate diagenesis in hypersaline environments: application of GC-IRMS to the stable isotope analysis of derivatized saccharides from surficial and buried sediments". Organic Geochemistry. 20 (7): 927–933. doi:10.1016/0146-6380(93)90104-J.
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