31883-92-8

Basic information

• Product Name: (S)-methyl 4-{[(benzyloxy)carbonyl]amino}-4-cyanobutanoate
• Synonyms: (S)-methyl 4-{[(benzyloxy)carbonyl]amino}-4-cyanobutanoate
• CAS NO: 31883-92-8
• Molecular Weight: 276.292
• Mol File: 31883-92-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-methyl 4-{[(benzyloxy)carbonyl]amino}-4-cyanobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 4-{[(benzyloxy)carbonyl]amino}-4-cyanobutanoate(31883-92-8)
• EPA Substance Registry System: (S)-methyl 4-{[(benzyloxy)carbonyl]amino}-4-cyanobutanoate(31883-92-8)

Safety Data

• Hazardous Substances Data: 31883-92-8(Hazardous Substances Data)

Upstream product

• 31883-94-0 N-(benzyloxycarbonyl)-L-γ-amino-γ-cyanobutyric acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 501-53-1 benzyl chloroformate 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 6398-06-7 N-benzyloxycarbonyl-L-isoglutamine 
• 51163-40-7 (S)-methyl 5-amino-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoate 

Downstream Products

• 96307-08-3 N-(benzyloxycarbonyl)-DL-(gln)Thz ethyl ester 
• 96391-81-0 N-Z-(R and S)(gln)Thz 
• 96307-07-2 N-(benzyloxycarbonyl)-L-γ-amino-γ-(thiocarbamoyl)butyramide 
• 96307-06-1 N-(benzyloxycarbonyl)-L-γ-amino-γ-cyanobutyramide 
• 95716-10-2 Z-L-(glu)Thz-OH 
• 31883-94-0 N-(benzyloxycarbonyl)-L-γ-amino-γ-cyanobutyric acid 

Relevant articles and documents

Acceptor-Controlled Transfer Dehydration of Amides to Nitriles

Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired scheme exergonic, thereby driving the dehydration.

Synthesis of the Dolastatin Thiazole Amino Acid Component (gln)Thz

The new thiazole amino acid (gln)Thz, found to occur as one unit of the marine sea hare cyclic pentapeptide dolastin 3, has been synthesized from L-glutamic acid by the route 2 -> 10e.The synthesis of Z-L-isoglutamine (4) was improved by selective ammonolysis of anhydride 3 at -60 deg C.A variety of reaction conditions were found to cause complete racemization during the Hantzsch thiazole synthesis step (9 -> 10).Deuterium labeling experiments indicated loss of the chiral center prior to formation of the thiazole system and suggested an imine-enamine type equilibration involving intermediates A B (Scheme II).The N-benzyloxycarbonyl derivative (10d) of (gln)Thz was partially resolved by employing brucine.