132957-40-5

Usage

InChI:InChI=1/C9H15NO4/c1-9(2,3)14-8(12)10-6-4-5-13-7(6)11/h6H,4-5H2,1-3H3,(H,10,12)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 
• 1192-20-7 2-aminobutyrolactone 
• 38308-92-8 2-(tert-butoxycarbonylamino)-4-hydroxy-butanoic acid 
• 135941-84-3 4-methyl (S)-N-tert-butoxycarbonylaspartate dicyclohexylammonium salt 
• 77856-40-7 (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate 
• 120042-11-7 methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate 
• 63-68-3 L-methionine 
• 2185-02-6 L-homoserine lactone 
• 61315-59-1 dicyclohexylamine salt of N-t-butyloxycarbonyl D-methionine 
• 74-88-4 methyl iodide 
• 110045-70-0 (R)-α-amino-γ-butyrolactone hydrobromide 
• 162107-48-4 tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate 
• 104347-13-9 (R)-(+)-α-amino-γ-butyrolactone hydrochloride 

Downstream Products

• 41088-86-2 L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid 
• 397246-14-9 (1-(hydroxymethyl)-3-hydroxypropyl)carbamic acid tert-butyl ester 
• 67198-78-1 (R)-2-tert-Butoxycarbonylamino-4-[4-(4-nitro-benzyloxyoxalyl)-phenoxy]-butyric acid benzhydryl ester 
• 745011-75-0 (R)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoic acid 
• 67198-88-3 BOC-D-homoserine diphenylmethyl ester 
• 92235-19-3 tert-butyl-(S)-(1-(benzylamino)-4-hydroxy-1-oxobutan-2-yl)-carbamate 
• 912846-42-5 1,1-dimethylethyl [(3S)-1-(2-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-2-oxo-3-pyrrolidinyl]carbamate 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 38308-92-8 2-(tert-butoxycarbonylamino)-4-hydroxy-butanoic acid 
• 132872-26-5 2-(tert-butoxycarbonylamino)-γ-butyrolactol 
• 156627-42-8 2-(tert-butoxycarbonylamino)butane-1,4-diol 

Relevant academic research and scientific papers

On the interactivity of complex synthesis and tumor pharmacology in the drug discovery process: Total synthesis and comparative in vivo evaluations of the 15-Aza epothilones

The total syntheses of 12,13,15-desoxy-15(S)-aza-epothilone B (aza-dEpoB; dEpoB-lactam) and 12,13,15-desoxy-15(R)-aza-epothilone B (15-epi-aza-dEpoB; 15-epi-dEpoB-lactam) have been accomplished via a highly convergent strategy. We have also successfully oxidized 12,13,15-desoxy-15(S)-aza-epothilone B to aza-epothilone B (aza-EpoB; EpoB-lactam). Aza-epothilone B has been advanced to phase I clinical trials by the Bristol-Myers Squibb group. Our synthesis is efficient and was amenable to the production of significant quantities of these lactams. Using our fully synthetically derived lactams, in vitro and in vivo studies were conducted in comparison with advanced clinical candidates, 12,13-desoxyepothilone B and 12,13-desoxyepothilone F, also derived by total synthesis.

Lithiation of N-Boc-2-methyltetrahydro-1,3-oxazine: A Synthetic Equivalent for 1-Lithio-3-hydroxy-1-propylamine

A α-metalo amine synthetic equivalent of an unactivated primary amine, 1-lithio-3-hydroxy-1-propylamine (7) is provided by the lithiation of N-Boc-2-methyltetrahydro-1,3-oxazine (8) to give 9 which on reaction with electrophiles and hydrolysis gives derivatives of 1-substituted 3-hydroxy-1-propylamines 10-24.

Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives

The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.

Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System

The Mitsunobu reaction is renowned for its mild reaction conditions and broad substrate tolerance, but has limited utility in process chemistry and industrial applications due to poor atom economy and the generation of stoichiometric phosphine oxide and hydrazine by-products that complicate purification. A catalytic Mitsunobu reaction using innocuous reagents to recycle these by-products would overcome both of these shortcomings. Herein we report a protocol that is catalytic in phosphine (1-phenylphospholane) employing phenylsilane to recycle the catalyst. Integration of this phosphine catalytic cycle with Taniguchi's azocarboxylate catalytic system provided the first fully catalytic Mitsunobu reaction. Make it catalytic: A catalytic Mitsunobu reaction using innocuous reagents to recycle the stoichiometric phosphine oxide and hydrazine by-products was developed. The reported method is catalytic in 1-phenylphospholane and uses phenylsilane to recycle the catalyst. Integration of this phosphine catalytic cycle with Taniguchi's azocarboxylate catalytic system provided the first fully catalytic Mitsunobu reaction.

Solution structural features of N-acyl homoserine lactones

Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e- withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (-1) contacts between N-acyl O and lactone C′. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues.

CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF

The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

Using the 9-BBN group as a transient protective group for the functionalization of reactive chains of α-amino acids

Achieving chemoselectivity is a longstanding challenge in chemical synthesis. This problem has been addressed using different approaches, but a definitive solution is still pending. For instance, in peptide chemistry, particularly with amino acids containing side chains functionalities with reactivity patterns similar to the main functional groups, such as aspartic and glutamic acids, and lysine and ornithine, specific semi-permanent protecting groups have been employed. The use of 9-borabicyclo[3.3.1]nonane (9-BBN-H) as a transient protective group for the selective protection of α-amino acids, which allows the chemoselective manipulation of the functional groups embedded in the side chains of the molecule, is described.

The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity

The preparation of a Syringolin A/Glidobactin A hybrid (SylA-GlbA) consisting of a SylA macrocycle connected to the GlbA side chain and its potent proteasome targeting of all three proteasomal subsites is reported. The influence of the syrbactin macrocycle moiety on subsite selectivity is demonstrated.

Ring opening of a trisubstituted aziridine with amines: Regio- and stereoselective formation of substituted 1,2-diamines

Figure Presented. The formation of substituted 1,2-diamines via nucleophilic ring opening of a trisubstituted ethynyl aziridine was performed with complete regio- and stereoselective control. Various amines with different levels of nucleophilicity were employed and gave similar results. The ring opening reaction is not limited to ethynyl aziridines, as other alkyl trisubstituted aziridines gave the same results. This method allows for the formation of unique vicinal diamines while providing a fully substituted carbon center in a stereoselective manner under mild conditions.