L-sucrose and process for producing same

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

C - Chemistry, Metallurgy

07

H

99/140, 260/233

C07H 3/04 (2006.01) A23L 1/22 (2006.01) A23L 1/236 (2006.01) C07C 29/10 (2006.01) C07C 43/178 (2006.01) C07C 205/15 (2006.01) C07D 321/06 (2006.01) C07D 493/18 (2006.01) C07H 3/02 (2006.01) C07H 15/04 (2006.01) C07H 15/18 (2006.01)

Patent

CA 1074308

Abstract L-sucrose or .beta.-?-fructofuranosyl .alpha.-?-glucopyranoside --(I), the enantiomer of naturally occuring ?-sucrose,which does not appear in nature has been synthesized and has been found to be sweet. It is unlikely that ?-sucrose is metabolized in the manner of ?-sucrose. In a preferred process for producing ?-sucrose the key step is the condensation of 2,3,4,6-tetra-0-benzyl- .alpha.-?-glucopyranosyl chloride --(II) with 1,3,4,6- tetra-O-benzyl-?-fructofuranose --(III). Compound II is obtained from ?-glucose by way of 2,3,4,6-tetra-0-benzyl- .alpha.-?-glucopyranose; and ?-glucose is prepared from ?-arabinose by nitromethane synthesis. Compound III is obtained by oxidation,with Jones reagent,of 1,3,4,6-tetra- O-benzyl-?-mannitol which, in turn, is prepared from ?-mannose. The condensation product of II and III is catalytically debenzylated to produce ?-sucrose.

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