144774-94-7

Upstream product

• 52396-85-7 Z-(S)-phenylalanine thioamide 
• 17157-48-1 bromoacetaldehyde 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 

Downstream Products

• 144775-04-2 Boc-(R)-dolaphenine 
• 120205-51-8 tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate 
• 130199-65-4 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine 
• 133565-36-3 2-<1'-((benzyloxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazole 
• 133565-36-3 (S)-benzyl 2-phenyl-1-(thiazol-2-yl)ethylcarbamate 

Relevant academic research and scientific papers

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.

Efficient stereoselective synthesis of dolastatin 10, an antineoplastic peptide from a sea hare

The stereoselective and efficient synthetic route to dolastatin 10, an antineoplastic peptide from a sea hare, has been developed. Dolaproine, one of the unusual constituents, was prepared in a highly stereoselective manner by the Evans aldol methodology.