148692-26-6

Basic information

• Product Name: Z-Val-Dil-Dap-Doe
• Synonyms: Z-Val-Dil-Dap-Doe
• CAS NO: 148692-26-6
• Molecular Weight: 792.053
• Mol File: 148692-26-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Z-Val-Dil-Dap-Doe(CAS DataBase Reference)
• NIST Chemistry Reference: Z-Val-Dil-Dap-Doe(148692-26-6)
• EPA Substance Registry System: Z-Val-Dil-Dap-Doe(148692-26-6)

Safety Data

• Hazardous Substances Data: 148692-26-6(Hazardous Substances Data)

Upstream product

• 132202-88-1 (3R,4S,5S)-4-(N-tert-butoxycarbonyl-N-methylamino)-3-methoxy-5-methyl-heptanoic acid 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 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 
• 133120-91-9 (2R,3R,4S)-dolaproine-(S)-dolaphenine 
• 120205-50-7 N-Boc-(2R,3R,4S)-dolaproine 
• 159173-43-0 (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 159173-40-7 (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 148597-90-4 Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 133565-36-3 2-<1'-((benzyloxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazole 

Downstream Products

• 110417-88-4 dolastatin 10 

Relevant articles and documents

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A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.