Abstract
Chemo‐Enzymatic Synthesis of Carbohydrates: The Preparation of L‐Xylose and 2‐Deoxy‐L‐xylo‐hexoseA synthetic approach to L‐xylose (6) and 2‐deoxy‐L‐xylo‐hexose (8) has been developed. The strategy utilizes achiral starting materials and employs two enzymatic reactions to introduce the desired chiral centers. Rabbit muscle aldolase (RAMA)‐catalyzed condensation of (3‐phenylthio)propanal (1) with dihydroxyacetone phosphate (DHAP) affords the C‐6 skeleton 2 with D‐threo configuration between C‐3 and C‐4. Diastereoselective reduction of 2 with sorbitol dehydrogenase (SDH) introduces the final stereocenter of the tetrahydroxy derivative 3. After oxidation of sulfide 3 to the corresponding diastereotopic sulfoxides 4, L‐xylose (6) is obtained by thermal elimination of phenylsulfenic acid followed by ozonolysis. 2‐Deoxy‐L‐xylo‐hexose (8) is yielded from 4 by a Pummerer rearrangement and subsequent reductive deprotection (DI‐BAL‐H) of the rearrangement product 7.
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