341489-97-2

Upstream product

• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 30379-55-6 benzyloxyacetic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 341490-01-5 C₂₈H₃₄O₈ 
• 182937-63-9 (R)-2-(benzyloxy)-3-phenylpropanoic acid 
• 100836-85-9 (R)-2-benzyloxypropionic acid 

Relevant academic research and scientific papers

A highly stereoselective entry to α-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary

Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate ester enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the (R)-configuration based upon comparisons to the literature. Both enantiomers of the auxiliary are readily available.

An inexpensive carbohydrate derivative used as a chiral auxiliary in the synthesis of α-hydroxy carboxylic acids

Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate (α-hydroxy acetate) enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the R configuration based on comparisons of optical rotations and on one crystal structure analysis. This alkylation methodology is compatible with several hydroxyl protecting groups. The free hydroxy acids were obtained upon removal of the protecting group from the hydroxyl functionality followed by saponification.