104227-71-6

Basic information

• Product Name: (S)-3-Boc-Amino-gamma-butyrolactone
• Synonyms: (S)-3-BOC-AMINOTETRAHYDROFURAN-5-ONE;(S)-3-BOC-AMINO-GAMMA-BUTYROLACTONE;(S)-3- BOC-AMINO -γ-BUTYROLACTONE;(S)-3-Boc-AMino-g-butyrolactone;CarbaMic acid, [(3S)-tetrahydro-5-oxo-3-furanyl]-, 1,1-diMethylethyl ester;(S)-3-Boc-AMino-GaMMa-ButyrolaCLone;tert-Butyl [(3S)-5-oxotetrahydrofuran-3-yl]carbamate;(S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbaMate
• CAS NO: 104227-71-6
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.22
• Product Categories: pharmacetical;Tetrahydrofuran Series
• Mol File: 104227-71-6.mol

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 363.7 °C at 760mmHg
• Flash Point: 173.8 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: 2-8°C
• PKA: 11.08±0.20(Predicted)
• CAS DataBase Reference: (S)-3-Boc-Amino-gamma-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Boc-Amino-gamma-butyrolactone(104227-71-6)
• EPA Substance Registry System: (S)-3-Boc-Amino-gamma-butyrolactone(104227-71-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 104227-71-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H15NO4/c1-9(2,3)14-8(12)10-6-4-7(11)13-5-6/h6H,4-5H2,1-3H3,(H,10,12)/t6-/m0/s1

Upstream product

• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 91240-51-6 N-tert-butyloxycarbonylaspartic acid anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 383418-08-4 3-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 13726-67-5 Boc-Asp-OH 
• 651036-12-3 [2-(R)-chloro-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 651035-90-4 (2-(R)-chloro-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 651035-84-6 2-(R)-tert-butoxycarbonylamino-3-chloro-propionic acid methyl ester 
• 651036-65-6 3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester 
• 83345-44-2 3-tert-butoxycarbonylamino-4-hydroxy-butyric acid 
• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 

Downstream Products

• 157823-89-7 [(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester 
• 368867-73-6 (αS,4S)-α-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid tert-butyl thioester 
• 221106-60-1 (S)-3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsiloxy)butyric acid benzyl ester 
• 83345-44-2 3-tert-butoxycarbonylamino-4-hydroxy-butyric acid 
• 834919-03-8 ((3S,4S)-4-Amino-5-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

In response to Berke?'s report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berke?'s revised structure.

Highly Functionalized Organolithium Reagents for Enantiomerically Pure α-Amino Acid Synthesis

(Equation presented) Highly functionalized L-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic α-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.

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.

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues.

DIAMINE DERIVATIVES

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

DIAMINE DERIVATIVES

A compound represented by the general formula (1):Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

A new entry to polyfunctionalized 4,5-trans disubstituted oxazolidin-2-ones from L-aspartic acid

A straightforward synthesis of enantiomerically pure (4R,5S)-5-oxazolidinecarboxylic acid, 2-oxo-4-[(t-butyldimethyl-silyloxy)methyl]-, benzyl ester and of (4S,5S)-4-oxazolidinecarboxylic acid, 2-oxo-5-[(t-butyldimethylsilyloxy)methyl]-, benzyl ester was envisaged starting from readily available L-aspartic acid. The key step is the diastereoselective addition of iodine with the introduction of a new stereogenic centre.

Syntheses of four unusual amino acids, constituents of cyclomarin A

The stereoselective syntheses of four unusual amino acids, constituents of cyclomarin A, are described. The protected N-methylhydroxyleucine 2 was synthesized using Evans' asymmetric azide-transfer reaction. The unusual amino acid 3 was prepared via diastereoselective methylation of the L-aspartic acid derived lactone 13. The stereoselective formation of threo-β-methoxyphenylalanine 4 was performed via aldol reaction using Scho?llkopf's chiral glycine enolate. The synthesis of N-reverse prenylated tryptophane 5 was achieved by the AQN ligand-promoted Sharpless regioreversed asymmetric aminohydroxylation protocol.