134221-95-7

Upstream product

• 120710-65-8 (1L)-1,2:5,6-Biscyclohexylidene-chiro-inositol 
• 25726-04-9 phenylglyoxylyl chloride 
• 134221-98-0 1L-1,2:5,6-di-O-cyclohexylidene-3-O-methoxymethyl-chiro-inositol 

Downstream Products

• 134222-02-9 1L-1,2:5,6-di-O-cyclohexylidene-3-O-<(2R)-2-hydroxy-2-phenylacetyl>-4-O-methoxymethyl-chiro-inositol 
• 134222-02-9 1L-1,2:5,6-di-O-cyclohexylidene-3-O-<(2S)-2-hydroxy-2-phenylacetyl>-4-O-methoxymethyl-chiro-inositol 
• 141039-25-0 C₂₉H₄₀O₉ 

Relevant academic research and scientific papers

Stereodivergent Synthesis of Optically Active α-Hydroxy Acids via Diastereoselective Reduction of α-Keto Esters Derived from L-Quebrachitol

Reduction of an α-keto ester derived from chiral cyclitol, readily available from L-quebrachitol, with K-Selectride proceeded via re-face attack of the ketone with high diastereoselectivity to obtain the α-hydroxy ester in 92percent de.On the other hand, reduction of the α-keto ester with K-Selectride in the presence of 18-Crown-6 took place via si-face attack of the ketone to furnish the corresponding α-hydroxy ester in 92percent de.Thus both enantiomers of mandelic acid were obtained in optically pure form.

Diastereoselective reduction of α-keto esters bearing chiro-inositol derivatives as chiral auxiliaries

The reduction of α-keto esters derived from (1L)-1,2;5,6-biscyclohexylidene-3-tert-butyldimethysilyl-chiro- inositol with Selectride proceeded with high diastereoselectivity to afford the corresponding α-hydroxy esters. Addition of 18-Crown-6 led to dramatic changeover in diastereofacial selectivity.