Xylitol pentacetate

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]

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

Synthesis

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

References
  1. 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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