Xylitol pentacetate

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
CAS Number	13437-68-8;
3D model (JSmol)	Interactive image;
ChemSpider	20000346;
PubChem CID	12939086;
	InChI 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;
	SMILES CC(=O)OC[C@H](C([C@H](COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C;
Properties
Chemical formula	C15H22O10
Molar mass	362.331 g·mol−1
Solubility in water	Soluble in water
Solubility	Soluble in methanol
	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]

^ ^a ^b ^c ^d 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.
^ 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.
^ 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. Bibcode:1993OrGeo..20..927M. doi:10.1016/0146-6380(93)90104-J.

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