80082-48-0

Basic information

• Product Name: t-butyloxycarbonyl-L-threonine amide
• CAS NO: 80082-48-0
• Molecular Weight: 218.253
• Mol File: 80082-48-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: t-butyloxycarbonyl-L-threonine amide(CAS DataBase Reference)
• NIST Chemistry Reference: t-butyloxycarbonyl-L-threonine amide(80082-48-0)
• EPA Substance Registry System: t-butyloxycarbonyl-L-threonine amide(80082-48-0)

Safety Data

• Hazardous Substances Data: 80082-48-0(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 60538-19-4 N-(tert-butoxycarbonyl)-l-threonine methyl ester 
• 2592-18-9 Boc-Thr-OH 
• 49705-99-9 (2S,3R)-2-amino-3-hydroxybutanamide 
• 72-19-5 L-threonine 

Relevant articles and documents

Synthesis method of aztreonam monocyclic mother nucleus

The invention discloses a synthesis method of an aztreonam monocyclic mother nucleus, and mainly relates to the technical field of pharmaceutical and chemical industry. The method comprises the stepsthat L-threonine is subjected to methyl esterification; terbutyloxycarbonyl anhydride is used for performing amino BOC protection; ammonia water is subjected to ammonolysis; under the catalysis of a solid basic catalyst, methyl-sulfuric-acyl reaction and sulfonation are performed; cyclization, deprotection and acidification are performed to obtain the aztreonam monocyclic mother nucleus. The raw materials are cheap and can be easily obtained; the yield is high; the cost is low; the synthesis method belongs to a green, energy-saving and environment-friendly practical technology.

An efficient procedure for the preparation of 4-substituted 5-aminoimidazoles

The preparation of O-methylimidates from α-aminonitriles and their subsequent co-cyclization with primary amines to afford 4-substituted 5-aminoimidazoles was studied. It was found that the mildly acidic pyridinium p-toluenesulfonate efficiently catalyzed each stage of the reaction sequence: (a) the formation of the O-methylimidates, (b) their co-cyclization with a variety of primary amines, and (c) certain derivatizations of the resultant heterocycles. The developed reaction conditions tolerate a wide variety of α-aminonitriles and primary amine co-reactants. Thus, it is possible to easily prepare a diverse array of substituted heterocyclic compounds in good yield. The requisite α-aminonitriles were synthesized either from amino acids or by phase-transfer alkylation of a glycine anion equivalent. The unstable free 5-aminoimidazoles were normally protected in situ to provide derivatives (methyl imidates or N,N-dimethylamidines) that were amenable to characterization.

4-alkylated monobactams. Chiral synthesis and antibacterial activity

The synthesis of 4-alkylated monobactams by a variety of procedures is described. Two complementary procedures have been developed for the chiral synthesis of monobactams: (1) sulfonation of 4-alkyl-3-(protected)amino-2-azetidinones with various complexes of SO3; and (2) cyclization of β-mesyloxyacyl sulfamates derived from β-alkyl-β-hydroxy-α-amino acids. The most general procedure involves introduction of the alkyl group via a Grignard reaction on 6-APA-derived sulfones 23 or 24 followed by sulfonation. For the specific case of (3S,trans-)-3-amino-4-methylmonobactamic acid (48), cyclization of the β-mesyloxyacyl sulfamate 40 derived from (L)-threonine is the preferred route. The introduction of 4-alkyl groups into monobactams results in a decrease in activity against gram-positive bacteria, an increase in activity against gram-negative bacteria, and an increase in β-lactamase stability. Increasing the size of the alkyl group beyond methyl results in diminished intrinsic antibacterial activity. 4β-Alkylmonobactams display better β-lactamase stability than their 4α-counterparts.