153668-71-4

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine
• Synonyms: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine
• CAS NO: 153668-71-4
• Molecular Weight: 473.637
• Mol File: 153668-71-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine(153668-71-4)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine(153668-71-4)

Safety Data

• Hazardous Substances Data: 153668-71-4(Hazardous Substances Data)

Upstream product

• 120205-50-7 N-Boc-(2R,3R,4S)-dolaproine 
• 158189-10-7 (+/-)-Boc-dolaphenine 
• 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 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 69610-41-9 Boc-L-Pro-H 
• 133565-36-3 2-<1'-((benzyloxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazole 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 

Downstream Products

• 159248-98-3 Boc-Dil-Dap-(R)-Doe 
• 159248-99-4 Z-Val-Dil-Dap-(R)-Doe 

Relevant articles and documents

The dolastatins. 22. Synthesis of Boc-dolaproinyl-dolaphenine and four related chiral isomers

Synthesis of the dolastatin 10 (1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3-5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosph

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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.