129866-72-4

Upstream product

• 121-39-1 ethyl cis-3-phenylglycidate 
• 130608-01-4 (2S,3R)-methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 129939-43-1 Sodium (+)-(2S,3S)-Z-3-phenyl oxirane-2-carboxylate 
• 54885-10-8 sodium (E)-3-phenylglycidate 

Downstream Products

• 119628-74-9 trans-(4S,5R)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 161759-90-6 (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 129939-53-3 Methyl (2R,3R)-3-phenyl-1H-aziridine-2-carboxylate 

Relevant academic research and scientific papers

Determination of the structure and its absolute configuration of 2″-hydroxynicotianamine, an inhibitor against Angiotensin-I converting enzyme in buckwheat, through the total synthesis

Nicotianamine is known as an inhibitor against Angiotensin-I Converting Enzyme (ACE). We synthesized a new nicotianamine derivative with an additional hydroxy group isolated from buckwheat (Fagopyrum esculentum Moench) powder and determined its regio and stereochemistry unambiguously by the enantioselective synthesis of diastereomers.

Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate

Sodium -E3-phenylglycidate (±)-2E was prepared using the Darzens' procedure. Classical resolution with 1-phenylethylamine afforded optically pure salts (+)-(2S,3R)-2E and (-)-(2R,3S)-2E. Alternatively, (±)-2E was converted into (±)-2Z by ring opening of ethyl ester (±)1E with hydrogen bromide, followed by recyclization and saponification. Classical resolution of (±)-2Z with ephedrine afforded optically pure salts (+)-(2S,3S)-2Z and (-)-(2R,3R)-2Z Treatment of the four sodium salts with sodium azide followed by esterification gave hydroxy azido esters 3, which were finally converted into the four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate 5 in a reaction with triphenylphosphine and subsequent heating of the initially formed oxazaphospholidines 4.