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A One-Pot Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by Hydrodeoxygenation of Xylose Using a Palladium Catalyst

A One-Pot Synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by Hydrodeoxygenation of Xylose Using a Palladium Catalyst

Michael A Jackson, Judith A Blackburn, Neil P J Price, Karl E Vermillion, Steven C Peterson, Gregory M Ferrence

Carbohydr Res. 2016 Sep 2;432:9-16.

PMID: 27341396

Abstract:

In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35-40% yield under 7 MPa H2 pressure at 733 K using 3-10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. (1)H and (13)C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K-273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP629594	Tetradecane		629-59-4	Price

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