226067-37-4

Basic information

• Product Name: Boc-N-Me-D-Thr(Bzl)-OH
• Synonyms: Boc-N-Me-D-Thr(Bzl)-OH
• CAS NO: 226067-37-4
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.38
• Product Categories: amino acids
• Mol File: 226067-37-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boc-N-Me-D-Thr(Bzl)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-N-Me-D-Thr(Bzl)-OH(226067-37-4)
• EPA Substance Registry System: Boc-N-Me-D-Thr(Bzl)-OH(226067-37-4)

Safety Data

• Hazardous Substances Data: 226067-37-4(Hazardous Substances Data)

Upstream product

• 69355-99-3 Boc-O-benzyl-D-threonine 
• 74-88-4 methyl iodide 

Downstream Products

• 474085-54-6 (2R,3S)-3-Benzyloxy-2-(tert-butoxycarbonyl-methyl-amino)-butyric acid benzyl ester 
• 1439366-92-3 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate 
• 1439367-96-0 (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid 
• 1439367-95-9 [(1R,2S)-1-carboxy-2-hydroxy-propyl]-methyl-ammonium toluene-4-sulfonate 
• 170872-87-4 (2R,3S)-2-[tert-butoxycarbonyl-(methyl)-amino]-3-hydroxy-butanoic acid 

Relevant articles and documents

Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3- oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors

N-Acylethanolamine acid amidase (NAAA) is a lysosomal cysteine hydrolase involved in the degradation of saturated and monounsaturated fatty acid ethanolamides (FAEs), a family of endogenous lipid agonists of peroxisome proliferator-activated receptor-α, which include oleoylethanolamide (OEA) and palmitoylethanolamide (PEA). The β-lactone derivatives (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide (2) and (S)-N-(2-oxo-3-oxetanyl)- biphenyl-4-carboxamide (3) inhibit NAAA, prevent FAE hydrolysis in activated inflammatory cells, and reduce tissue reactions to pro-inflammatory stimuli. Recently, our group disclosed ARN077 (4), a potent NAAA inhibitor that is active in vivo by topical administration in rodent models of hyperalgesia and allodynia. In the present study, we investigated the structure-activity relationship (SAR) of threonine-derived β-lactone analogues of compound 4. The main results of this work were an enhancement of the inhibitory potency of β-lactone carbamate derivatives for NAAA and the identification of (4-phenylphenyl)-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate (14q) as the first single-digit nanomolar inhibitor of intracellular NAAA activity (IC50 = 7 nM on both rat NAAA and human NAAA).

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

A highly convergent asymmetric synthesis of the protein phosphatase inhibitor motuporin 1a is described. Synthesis and coupling of the individual peptide fragments [34 + -35 → 51] followed by macrocyclization afforded the fully protected motuporin precursor 33, which is converted to the natural product by dehydration and ester hydrolysis, Six of the eight stereogenic centers associated with the natural product were introduced using asymmetric crotylsilane bond construction methodology. Our approach features an efficient Pd(0)-catalyzed cross-coupling reaction between a configurationally well-defined vinyl zinc intermediate 22 and an (E)-vinyl iodide 7, which afforded compound 43, resulting in the construction of the trisubstituted (E,E)-diene system of the motuporin side chain. Improved reaction conditions for macrocyclization in the formation of 33 are also detailed.