THE ISOMERIC TETRACETATES OF XYLOSE, AND OBSERVATIONS

J. Am. Chem. Soc. , 1915, 37 (12), pp 2748–2753. DOI: 10.1021/ja02177a023. Publication Date: December 1915 .... Published online 1 May 2002. Publish...
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2748

C. S . HUDSON AND J. M. JOHNSON.

[CONTRIBUTION FROM THE CARBOHYDRATE LABORATORY, BUREAUOF CHEMISTRY, UNITEDSTATES USPARTXENT OF AGRICULTURE. ]

THE ISOMERIC TETRACETATES OF XYLOSE, AND OBSERVATIONS REGARDING THE ACETATES OF MELIBIOSE, TREHALOSE AND SUCROSE. HY C S. HUDSONA X D J. M .

JOHNSON

Received September 11. 1915.

Crystalline xylose tetracetate has been prepared by Stone' through the action of acetic anhydride and sodium acetate upon the sugar, and he records its melting point as 123.j-4.5 and its specific rotation in absolute alcohol -25.43 '. Bader3 has found the substance to melt slightly higher, 126'. We have recently converted this tetracetate to an isomeric form hy heating it in acetic anhydride solution with a trace of zinc chloride, as will presently be described. The new tetracetate and the one prepared by Stone represent a pair of isomers similar to the alpha and beta forms of the pentacetates of mannose and glucose and the octacetates of cellose, maltose and lactose, and their structures may accordingly be written, assuming a gamma lactonyl ring, /OAC

and CH2OAc.CH.(CH0Ac)s.C

CHpOAc.CH.(CH0Ac)s.C

-o------I

\H

-o-----I