709656-15-5

Upstream product

• 99184-99-3 2-phenyloxazoline-4-carboxylic acid 
• 116956-53-7 sodium 2-phenyloxazoline-4-carboxylate 
• 100-47-0 benzonitrile 
• 55044-06-9 methyl 2-phenyl-2-oxazoline-4-carboxylate 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 100-39-0 benzyl bromide 
• 709656-07-5 2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester 

Downstream Products

• 1613450-05-7 tert-butyl 2-benzyl-2-(benzylamino)-3-hydroxypropanoate 
• 1613450-08-0 tert-butyl 3,4-dibenzyl-2-oxo-1,2,3-oxathiazolidine-4-carboxylate 
• 1613450-11-5 tert-butyl 3,4-dibenzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate 
• 1613450-01-3 tert-butyl 2-benzylamino-3-((R)-2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropylthio)-2-ethylpropanoate 
• 51127-30-1 (+/-)-α-benzylserine 

Relevant academic research and scientific papers

An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: Practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

Practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The α-alkylation and β-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives α-alkylation (up to >99%), and t-BuOK in DMF gives β-elimination (98%).

Synthesis of protected α-alkyl lanthionine derivatives

Protected α-alkyl lanthionine derivatives were synthesized in five steps starting from a known phenyloxazoline precursor. This approach involved the synthesis of a family of substituted cyclic sulfamidates and their regioselective opening by nucleophilic attack with a protected cysteine. This efficient multistep strategy affords various α-alkylated lanthionine derivatives in high yields.