137396-20-4

Upstream product

• 108-98-5 thiophenol 
• 27098-65-3 3-phenylsulfanyl-propionaldehyde 
• 108-24-7 acetic anhydride 
• 137396-19-1 5-Desoxy-6-S-phenyl-6-thiofructose 

Downstream Products

• 154-58-5 1,5-anhydro-D-glucitol 
• 137396-22-6 1,3,4,5,6-Penta-O-acetyl-2-desoxy-L-gulo-S-phenyl-hemithioacetal 
• 194991-50-9 (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 137396-21-5 1,2,3,4-Tetra-O-acetyl-5,6-didesoxy-6-phenylsulfinyl-D-xylohexitol 

Relevant academic research and scientific papers

Chemo-Enzymatic Synthesis of Carbohydrates: The Preparation of L-Xylose and 2-Deoxy-L-xylo-hexose

A 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 (DIBAL-H) of the rearrangement product 7. Key Words: L-Xylose / 2-Deoxy-L-xylo-hexose / Enzymatic syntheses / Carbohydrates