54984-42-8

Upstream product

• 69217-50-1 t-Butyl β-methyl-β-phenylglycidic ester 

Downstream Products

• 76527-42-9 (2S,3R)-3-Methyl-3-phenyl-oxirane-2-carbonyl chloride 
• 89849-04-7 (2R,3S)-3-Methyl-3-phenyl-oxirane-2-carbonyl azide 
• 76527-42-9 (2R,3R)-3-Methyl-3-phenyl-oxirane-2-carbonyl chloride 
• 66364-96-3 C₁₃H₁₄O₅ 

Relevant academic research and scientific papers

Convenient synthesis of t-butyl Z-3-substituted glycidates under conditions of phase-transfer catalysis

Reactions of mixtures of t-butyl E- and Z-3-substituted glycidates 1a-h with 50% aq. sodium hydroxide and a catalyst, benzyltriethylammonium chloride, TEBAC in dichloromethane (phase-transfer catalysis, PTC) led to preferential hydrolysis of the E-isomers to afford pure (90-98%) t-butyl Z-3-substituted glycidates 1a-i in good yields; PTC cleavage of glycidates additionally substituted at C-2, 1g or C-3, 1h,i suggests that an aryl group in the Z isomers hampers attack of HO- on the carbonyl carbon atom. As described in the literature, the diastereoselective PTC synthesis of Z-3-substituted glycidates and glycidonitriles consists of fast hydrolysis of E isomers present in mixtures with Z ones.