120205-64-3

Upstream product

• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 60-23-1 Cysteamine 
• 156-57-0 2-mercaptoethylamine hydrochloride 

Downstream Products

• 135383-62-9 Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 110417-88-4 dolastatin 10 
• 135383-61-8 Cbz-Dil-Dap-Doe 
• 159173-45-2 (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 120205-54-1 tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate 
• 135383-60-7 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethanamine, hydrochloride salt 
• 133120-91-9 (2R,3R,4S)-dolaproine-(S)-dolaphenine 
• 120205-51-8 tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate 
• 142342-91-4 (S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-3-thiazoline 
• 144775-04-2 Boc-(R)-dolaphenine 

Relevant academic research and scientific papers

The Dolastatins 16. Synthesis of Dolaphenine

Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized.While conversion (4 -> 7 or 4 -> 11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventfu

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.

An expeditious synthesis of dolastatin 10

Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.