148597-90-4

Basic information

• Product Name: Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe
• Synonyms: Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe
• CAS NO: 148597-90-4
• Molecular Weight: 658.903
• Mol File: 148597-90-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe(148597-90-4)
• EPA Substance Registry System: Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe(148597-90-4)

Safety Data

• Hazardous Substances Data: 148597-90-4(Hazardous Substances Data)

Upstream product

• 133565-36-3 2-<1'-((benzyloxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazole 
• 133645-49-5 (3R,4S,5S )-ethyl 4-((tert-butoxycarbonyl)amino)-3-hydroxy-5-methyl-heptanoate 
• 133565-39-6 (4S,5S)-ethyl 4-((tert-butoxycarbonyl)amino)-5-methyl-3-oxo-heptanoate 
• 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 
• 135383-59-4 ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate 
• 120205-50-7 N-Boc-(2R,3R,4S)-dolaproine 
• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 944728-66-9 ethyl (3R,4S,5S)-4-(N-tert-butoxycarbonyl-N-methylamino)-3-methoxy-5-methyl-heptanoate 
• 132202-88-1 (3R,4S,5S)-4-(N-tert-butoxycarbonyl-N-methylamino)-3-methoxy-5-methyl-heptanoic acid 
• 133120-91-9 (2R,3R,4S)-dolaproine-(S)-dolaphenine 
• 133645-51-9 (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 133565-36-3 (S)-benzyl 2-phenyl-1-(thiazol-2-yl)ethylcarbamate 
• 133565-38-5 (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid 
• 120205-51-8 tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate 

Downstream Products

• 148692-26-6 Z-Val-Dil-Dap-Doe 
• 135383-62-9 Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 110417-88-4 dolastatin 10 
• 159173-45-2 (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 

Relevant articles and documents

Total synthesis of dolastatin 10 through ruthenium-catalyzed asymmetric hydrogenations

A total synthesis of dolastatin 10, a potent inhibitor of microtubule assembly, which displayed remarkable antineoplastic activity, is reported. Our synthetic approach was based upon ruthenium-promoted asymmetric hydrogenation of β-keto esters derived from (S)-Boc-proline and (S)-Boc-isoleucine for the construction of the two key units: (2R,3R)-Boc-dolaproine (Dap) and (3R)-Boc-dolaisoleucine (Dil).

Stereoselective Synthesis of Dolastatin 10 and Its Congeners

Efficient synthesis of dolastatin 10 (1), a potent antitumor peptide from a sea hare Dolabella auricularia, has been achieved in a stereoselective manner.Trisnordolastatin 10 (2) and its C9-epimer (3) have also been synthesized.