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

• 66543-86-0 (S)-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid sodium salt 
• 24424-99-5 di-tert-butyl dicarbonate 
• 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 
• 2185-02-6 L-homoserine lactone 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 91240-51-6 N-tert-butyloxycarbonylaspartic acid anhydride 
• 34619-03-9 tert-butyldicarbonate 
• 77856-40-7 (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate 
• 135941-84-3 4-methyl (S)-N-tert-butoxycarbonylaspartate dicyclohexylammonium salt 
• 41088-86-2 L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid 

Downstream Products

• 105183-60-6 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 
• 77856-40-7 (S)-2-oxotetrahydrofuran-3-aminium trifluoroacetate 
• 1028258-40-3 (S)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid 
• 264277-28-3 (S)-2-(tert-butoxycarbonylamino)-4-hydroxy-N-pyridin-2-ylbutyramide 
• 264277-36-3 [3-hydroxy-1-(thiazol-2-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-37-4 [3-hydroxy-1-(isoxazol-3-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-29-4 [3-hydroxy-1-(pyridin-3-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-32-9 [3-hydroxy-1-(pyrimidin-4-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-30-7 [3-hydroxy-1-(pyridin-4-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-31-8 [3-hydroxy-1-(pyrazin-2-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-38-5 tert-butyl N-[(1S)-3-hydroxy-1-[[(3R)-tetrahydrofuran-3-yl]carbamoyl] propyl] carbamate 
• 264277-34-1 [3-hydroxy-1-(quinolin-5-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-33-0 [3-hydroxy-1-(isoquinolin-5-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 264277-35-2 [3-hydroxy-1-(4-morpholin-4-yl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 

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.

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.

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.