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. 2009 Jan 31;65(Pt 2):o414-5.
doi: 10.1107/S1600536809002876.

(1S)-1,2-O-Benzyl-idene-α-d-glucurono-6,3-lactone

Sarah F Jenkinson, Daniel Best, Alexander C Weymouth-Wilson, Robert A Clarkson, George W J Fleet, David J Watkin

(1S)-1,2-O-Benzyl-idene-α-d-glucurono-6,3-lactone

Sarah F Jenkinson et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

X-ray crystallographic analysis has established that the major product from the protection of d-glucoronolactone with benzaldehyde is (1S)-1,2-O-benzyl-idene-α-d-glucurono-6,3-lactone, C(13)H(12)O(6), rather than the R epimer. The crystal structure exists as O-H⋯O hydrogen-bonded chains of mol-ecules lying parallel to the a axis. The absolute configuration was determined by the use of d-glucuronolactone as the starting material.

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Figures

Fig. 1.
Fig. 1.
Synthetic scheme
Fig. 2.
Fig. 2.
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
Fig. 3.
Fig. 3.
Packing diagram of the title compound projected along the b-axis. Hydrogen bonding is indicated by dotted lines.
Fig. 4.
Fig. 4.
Packing diagram showing alternating layers of hydrogen bonded chains of molecules.
See this image and copyright information in PMC

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