40856-59-5

Basic information

• Product Name: (S)-(-)-alpha-(Boc-Amino)-gamma-butyrolactone
• Synonyms: (S)-(-)-ALPHA-(N-T-BOC-AMINO)-GAMMA-BUTYROLACTONE;(S)-2-BOC-AMINO-GAMMA-BUTYROLACTONE;(R)-2-BOC-AMINO-GAMMA-BUTYROLACTONE;(S)-(-)-alpha-(N-t-boc-Amino)-b-butyrolactone;(S)-(-)-ALPHA-(N-TERT-BOC-AMINO)-BETA-BUTYROLACTONE;(S)-tert-butyl 2-oxo-tetrahydrofuran-3-ylcarbamate;(S)-(-)-a-(Boc-Amino)-g-butyrolactone;(S)-(-)-a-(N-t-BOC-Amino)-butyrolactone
• CAS NO: 40856-59-5
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.22
• Product Categories: amino acids
• Mol File: 40856-59-5.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 363.7 °C at 760 mmHg
• Flash Point: 173.8 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 1.77E-05mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: 2-8°C
• PKA: 11.21±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-alpha-(Boc-Amino)-gamma-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-alpha-(Boc-Amino)-gamma-butyrolactone(40856-59-5)
• EPA Substance Registry System: (S)-(-)-alpha-(Boc-Amino)-gamma-butyrolactone(40856-59-5)

Safety Data

• Hazardous Substances Data: 40856-59-5(Hazardous Substances Data)

Usage

Uses

(S)-(-)-α-(N-t-BOC-Amino)-γ-butyrolactone is used in the preparation of N-acyl homoserine lactones as interbacterial quorum signal modulators as antibacterial agents.

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)/t6-/m0/s1

Upstream product

• 41088-86-2 L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 77856-40-7 (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate 
• 2185-03-7 L-homoserine lactone hydrochloride 
• 120042-11-7 methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 224192-24-9 methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-hydroxybutanoate 
• 63-68-3 L-methionine 
• 34619-03-9 tert-butyldicarbonate 
• 2185-02-6 L-homoserine lactone 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 91240-51-6 N-tert-butyloxycarbonylaspartic acid anhydride 
• 135941-84-3 4-methyl (S)-N-tert-butoxycarbonylaspartate dicyclohexylammonium salt 
• 66543-86-0 (S)-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid sodium salt 

Downstream Products

• 1028258-40-3 (S)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid 
• 189017-50-3 ((S)-1-Dimethylcarbamoyl-3-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 902468-35-3 (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butyrolactone 
• 553652-15-6 1,1-dimethylethyl ((1S)-1-{[(2-fluoro-4-iodophenyl)amino]carbonyl}-3-hydroxypropyl)-carbamate 
• 912846-41-4 1,1-dimethylethyl ((1S)-3-hydroxy-1-{[(2-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)amino]carbonyl}propyl)carbamate 
• 553652-14-5 C₁₄H₂₀IN₃O₄ 
• 1007887-07-1 C₁₅H₂₀BrFN₂O₄ 
• 553652-17-8 tert-butyl (3S)-1-(2-fluoro-4-iodophenyl)-2-oxopyrrolidin-3-ylcarbamate 
• 553652-21-4 C₂₁H₂₈FN₅O₃ 
• 147325-09-5 N-Boc-L-homoserine ethyl ester 
• 811788-87-1 phenylmethyl 4-[(N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-homoseryl)amino]-3-fluorobenzoate 
• 811799-63-0 1,1-dimethylethyl {(1S)-1-[({4-[(1S)-1-(dimethylamino)ethyl]-2-fluorophenyl}amino)carbonyl]-3-hydroxypropyl}carbamate 
• 811799-73-2 1,1-dimethylethyl {(1S)-1-[({4-[(1R)-1-(dimethylamino)ethyl]-2,6-difluorophenyl}amino)carbonyl]-3-hydroxypropyl}carbamate 
• 1293979-64-2 C₂₀H₂₈FN₃O₃ 

Relevant articles and documents

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.

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.

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.