32975-58-9

Basic information

• Product Name: (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone
• Synonyms: (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone
• CAS NO: 32975-58-9
• Molecular Weight: 309.324
• Mol File: 32975-58-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone(32975-58-9)
• EPA Substance Registry System: (R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone(32975-58-9)

Safety Data

• Hazardous Substances Data: 32975-58-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 17609-52-8 Z-D-phenylglycine 
• 501-53-1 benzyl chloroformate 
• 875-74-1 (R)-phenylglycine 

Downstream Products

• 83649-47-2 (S)-(-)-β-Phenyl-β-alanine hydrochloride 
• 32975-59-0 methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate 
• 14441-08-8 (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid 

Relevant articles and documents

Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes

An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth

Synthesis of the Alkaloid Homaline in (+/-) and Natural (S,S)-(-) Forms, using Amination and Transamidative Ring Expansion in Liquid Ammonia

Synthesis of the alkaloid homaline in (+/-) and natural (S,S)-(-) forms is reported.Linking of 2-azacyclooctanone units either directly or successively using 1,4-dihalogenobutanes or 1,4-dihalogenobut-2-ynes is examined. (+/-)-5-Methyl-4-phenyl-1,5-diazacyclooctan-2-one is first made by a 2,2'-dithiodipyridine/triphenylphosphine-mediated cyclisation, and then by amination and transamidative ring expansion from N-(3-chloropropyl)-4-phenylazetidin-2-one in liquid ammonia, followed by N-methylation.Coupling through a 1,4-dihalogenobutane of either the N-methylated azalactam, or the unmethylated azalactam followed by methylation, gave homaline in (+/-) and meso forms. (R)-(-)-Phenylglycine was converted via (S)-β-phenyl-β-alanine into an (S)-β-lactam which was then alkylated with 1-bromo-3-chloropropane, and aminated and ring expanded in liquid ammonia.Coupling of the homochiral azalactam (2 mol) so formed with 1,4-dibromobutane, followed by N-methylation, gave (S,S)-(-)-homaline identical with the natural material.