L-Sucrose and process for producing same

Details L-Sucrose and process for producing same L-Sucrose and process for producing same

1978-04-13

1980-06-10

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 4, 536122, C07H 304

Patent

active

042074134

ABSTRACT:
L-sucrose or .beta.-L-fructofuranosyl .alpha.-L-glucopyranoside--(I), the enantiomer of naturally occuring D-sucrose, which does not appear in nature has been synthesized and has been found to be sweet. It is unlikely that L-sucrose is metabolized in the manner of D-sucrose. In a preferred process for producing L-sucrose the key step is the condensation of 2,3,4,6-tetra-O-benzyl-.alpha.-L-glucopyranosyl chloride--(II) with 1,3,4,6-tetra-O-benzyl-L-fructofuranose--(III). Compound II is obtained from L-glucose by way of 2,3,4,6-tetra-O-benzyl-.alpha.-L-glucopyranose; and L-glucose is prepared from L-arabinose by nitromethane synthesis. Compound III is obtained by oxidation, with Jones reagent, of 1,3,4,6-tetra-O-benzyl-L-mannitol which, in turn, is prepared from L-mannose. The condensation product of II and III is catalytically debenzylated to produce L-sucrose.

REFERENCES:
Lemieux, R., et al., J. Am. Chem. Soc. 78, 4117 (1956).
Hassid and Ballou, "The Carbohydrates", Pigman, Ed., Academic Press Inc., New York, 1957, p. 483.
Berry et al., "Chem. Abst.", vol. 82, 1975, 98280g.
King et al., "Chem. Abst.", vol. 83, 1975, 179439p.

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