757232-69-2

Upstream product

• 163960-83-6 (4S,5R)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 
• 62317-42-4 ethyl (+/-)-3-acetoxy-2-bromo-3-phenylpropanoate 
• 108741-12-4 ethyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate 
• 163893-32-1 (4S,5R)-2-Oxo-5-phenyl-2λ⁴-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 

Downstream Products

• 115794-66-6 trans-methyl 3-phenylglycidate 
• 121-39-1 (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate 

Relevant academic research and scientific papers

Chemoenzymatic approach to optically active phenylglycidates: Resolution of bromo- and iodohydrins

Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem, were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched (2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein, including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)-phenylglycidates.

Stereoselective chemoenzymatic process for the preparation of optically enriched phenylglycidates as precursors of taxol side chain

The present invention relates to a novel and efficient chemoenzymatic process of preparation of optically active trans alkyl phenylglycidates. The invention particularly discloses a novel process for the chemoenzymatic synthesis of two enantiomers of tran

Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate

An efficient synthesis of chiral α,β-epoxyester 1 from chiral 2,3- dihydroxyester 2 has been developed. Ester 2 is converted to the corresponding cyclic surfate 3, which is opened with either LiBr in THF or Bu4NBr in acetone at rt to furnish 2-bromo-3-hydroxyester 4. Treatment of 4 with K2CO3 in methanol at low temperature gives α,β-epoxyester 1 in excellent overall yield and in the same ee as in the starting diol.