144775-04-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 130199-65-4 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine 
• 144774-97-0 [R-(-)-2-phenyl-1-(2-thiazolyl)ethylamine] 
• 185986-59-8 (+/-)-dolaphenine 
• 144831-03-8 (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-ol 
• 144774-94-7 [1-(4-Hydroxy-4,5-dihydro-thiazol-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 144775-06-4 2-[(1S)-1-azido-2-phenylethyl]-1,3-thiazole 
• 133565-36-3 (S)-benzyl 2-phenyl-1-(thiazol-2-yl)ethylcarbamate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 52396-85-7 Z-(S)-phenylalanine thioamide 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 179077-79-3 ((R)-2-Phenyl-1-thiazol-2-yl-ethyl)-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-amine 
• 179238-80-3 (1S,2S,5S)-2,6,6-Trimethyl-3-[(E)-(R)-2-phenyl-1-thiazol-2-yl-ethylimino]-bicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 

Relevant academic research and scientific papers

Addition of 2-lithiothiazoles to ROPHy/SOPHy aldoximes: Asymmetric synthesis of 1-(2-thiazolyl)ethylamines

A new asymmetric synthesis of 1-(2-thiazolyl)ethylamines is described in which the key step is the diastereoselective addition of 2-lithiothiazoles to O-(1-phenylbutyl) aidoximes.

Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles

A method is described for the enantioselective synthesis of 2-(1-aminoalkyl)thiazoles 6 via stereoselective alkylation of the carbanions of (+)-(R)-camphor and (-)-(1S, 2S, 5S)-2-hydroxypinan-3-one imines 2 and 3 derived from 2-(aminomethyl)thiazole (2-AMT, 1). Compounds 6 serve as α-amino aldehyde precursors via thiazolyl-to-formyl conversion.

A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10

Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.