113775-22-7

Basic information

• Product Name: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE
• Synonyms: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE;N-T-BOC-4-HYDROXY-L-PYRROLIDINE LACTONE;(1S,4S)-tert-Butyl-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate;N-Boc-4-hydroxy-L-pyrrolidine lactone;N-Boc-5-aza-2-oxa-3-oxo-bicyclo[2.2.1]heptane;(1S,4S)-3-Oxo-2-Oxa-5-Azabicyclo[2.2.1]Heptane-5-carboxylic Acid 1,1-Dimethylethyl Ester
• CAS NO: 113775-22-7
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.23
• Mol File: 113775-22-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 109-114°C
• Boiling Point: 349.7°C at 760 mmHg
• Flash Point: 165.3°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 4.63E-05mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.25±0.20(Predicted)
• CAS DataBase Reference: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE(113775-22-7)
• EPA Substance Registry System: BOC-4-HYDROXY-L-PYRROLIDINE LACTONE(113775-22-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 113775-22-7(Hazardous Substances Data)

Usage

General Description

BOC-4-HYDROXY-L-PYRROLIDINE LACTONE is a chemical compound with the molecular formula C9H15NO3. It is a lactone derivative with a Boc (tert-butoxycarbonyl) protected amino group and a hydroxyl group. BOC-4-HYDROXY-L-PYRROLIDINE LACTONE is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and fine chemicals. It is also utilized as a key intermediate in the synthesis of drugs and pharmaceutical compounds. BOC-4-HYDROXY-L-PYRROLIDINE LACTONE is a valuable compound for the production of a wide range of pharmaceutical products due to its versatile reactivity and functional groups.

InChI:InChI=1/C10H15NO4/c1-10(2,3)15-9(13)11-5-6-4-7(11)8(12)14-6/h6-7H,4-5H2,1-3H3/t6-,7-/m0/s1

Upstream product

• 202477-59-6 (2S,4R)-1-(tert-butoxycarbonyl)-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 1332341-02-2 benzyl (2S)-2-Boc-amino-3-(2-oxiranyl)propionate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 1434818-13-9 benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester 
• 1434818-32-2 benzenesulfonic acid (3S,5S)-5-(1-cyanocyclopropylcarbamoyl)-1-(1-methylcyclopropanecarbonyl)pyrrolidin-3-yl ester 
• 40350-83-2 (2S,4S)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 121148-00-3 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate 
• 1252637-36-7 (2S,4R)-4-(4-bromo-2-trifluoromethylbenzenesulfonyl)-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1252637-02-7 (2S,4R)-4-(4-fluoro-2-trifluoromethylbenzenesulfonyl)-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 

Relevant articles and documents

Solid-phase synthesis of a novel phalloidin analog with on-bead and off-bead actin-binding activity

Specific effectors of actin polymerization have found use as dynamic probes of cellular morphology that may be used to gauge cellular response to stimuli and drugs. Of various natural products that target actin, phalloidin is one of the most potent and selective inhibitors of actin depolymerization. Phalloidin and related members of the phallotoxin family are macrocyclic heptapeptides bearing a characteristic and rigidifying transannular tryptathionine bridge. Here we describe a solid-phase synthesis of a new phalloidin analog as a prototype for library development with the potential for on- and off-bead screening. To validate our method, we labelled the phalloidin derivative with a fluorescent dye which stained actin in CHO cells. Furthermore, a bioassay was developed allowing actin polymerization on beads carrying a phalloidin derivative.

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.

cis-4-Alkoxydialkyl- and cis-4-Alkoxydiarylprolinol Organocatalysts: High Throughput Experimentation (HTE)-Based and Design of Experiments (DoE)-Guided Development of a Highly Enantioselective aza-Michael Addition of Cyclic Imides to α,β-Unsaturated Aldehydes

A diverse family (37 compounds) of cis-4-alkoxydiorganylprolinol derivatives has been prepared and evaluated in organocatalysis for the first time. The combined use of high throughput experimentation (HTE) techniques with efficient analytical methods has led to the identification of two superior catalysts for the enantioselective addition of succinimide to α,β-unsaturated aldehydes. Further optimization of the reaction conditions with design of experiments (DoE) techniques established the catalyst of choice for the considered aza-Michael reaction, the corresponding adducts (12 examples) being obtained in good yields and excellent enantioselectivities (succinimide and maleimide donors). The synthetic versatility of these Michael adducts is illustrated by a two-step sequence leading to enantiopure 1,3-amino alcohols. (Figure presented.).