133565-36-3

Upstream product

• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 144774-94-7 [(S)-1-(4-Hydroxy-4,5-dihydro-thiazol-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 1394369-60-8 C₃₀H₃₄N₂O₈S 
• 1394369-61-9 C₃₆H₃₈N₂O₇S₂ 
• 1394369-62-0 Cbz-Phe-Cys-SPh 
• 1394369-55-1 C₂₆H₂₄N₂O₃S₂ 
• 1394369-56-2 Cbz-Phe-Cys(Trt)-OAllyl 
• 1394369-57-3 C₂₃H₂₄N₂O₄S 
• 1394369-58-4 C₂₀H₂₀N₂O₄S 
• 107-20-0 2-chloroethanal 
• 52396-85-7 Z-(S)-phenylalanine thioamide 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 144774-94-7 [1-(4-Hydroxy-4,5-dihydro-thiazol-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 

Downstream Products

• 133120-91-9 (2R,3R,4S)-dolaproine-(S)-dolaphenine 
• 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 
• 159173-45-2 (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 110417-88-4 dolastatin 10 
• 135383-62-9 Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 148597-90-4 Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 148616-85-7 Boc-(2S,3R,4S)-norDap-(S)-Doe 
• 148565-06-4 Boc-(2R,3R,4S)-norDap-(S)-Doe 
• 148565-08-6 Boc-(3R,4S,5S)-bisnorDil-(2S,3R,4S)-norDap-(S)-Doe 
• 148683-12-9 Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe 
• 144775-04-2 Boc-(R)-dolaphenine 
• 120205-51-8 tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate 

Relevant academic research and scientific papers

Biomimetic synthesis of Cbz-(S)-dolaphenine

A new route to Cbz-(S)-dolaphenine, a recurring element in bioactive peptidic natural products, has been implemented, which closely parallels the biogenetic pathway. Cyclodehydration of 11 to yield thiazoline 2 allows for a Ni(0)-promoted decarbonylative aromatization to provide the thiazole framework with retention of stereochemistry.

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.