19689-97-5

Usage

Uses

Used in Personal Care and Cosmetic Industry:
Tert-butyl hydroxy(methyl)carbamate is used as a preservative in various personal care and cosmetic products for its ability to inhibit bacterial and mold growth, ensuring the safety and longevity of these products.
Used in Lotions and Creams:
In lotions and creams, tert-butyl hydroxy(methyl)carbamate is used as a preservative to prevent microbial contamination, ensuring the product remains safe for use over time.
Used in Shampoos:
Tert-butyl hydroxy(methyl)carbamate is used in shampoos as a preservative to maintain the product's integrity and prevent the proliferation of bacteria and mold, which can cause spoilage and reduce the product's effectiveness.
Used in Soaps:
In soaps, tert-butyl hydroxy(methyl)carbamate is utilized as a preservative to prevent bacterial and mold growth, ensuring the soap remains hygienic and effective throughout its usage.
It is crucial for consumers to use products containing tert-butyl hydroxy(methyl)carbamate responsibly and in accordance with the manufacturer's instructions to minimize potential adverse effects and environmental impact.

Upstream product

• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 74-88-4 methyl iodide 
• 79722-22-8 N-methyl-2-{[(benzyloxy)carbamoyl]oxy}-2-methylpropylidyne 
• 593-77-1 N-Methylhydroxylamine 
• 34619-03-9 tert-butyldicarbonate 
• 71872-03-2 tert-Butyl-carbamic acid tert-butyl ester 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1237528-54-9 6,9,9-trimethyl-7-oxo-5,8-dioxa-2,6-diazadecanoic acid phenylmethyl 
• 1237528-55-0 7,10,10-trimethyl-8-oxo-6,9-dioxa-2,7-diazaundecanoic acid phenylmethyl ester 
• 79722-22-8 N-methyl-2-{[(benzyloxy)carbamoyl]oxy}-2-methylpropylidyne 
• 38100-38-8 tert-butyl (2,4-dinitrophenoxy)(methyl)carbamate 
• 1448581-76-7 tert-butyl 2,4-dinitrophenylsulfonyloxy(methyl)carbamate 
• 1440756-16-0 tert-butyl methyl((2,4,6-trichlorobenzoyl)oxy)carbamate 
• 1217264-32-8 N-(2-Boc-aminoethyl)-4-[(N-Boc-N-methylaminooxy)methyl]benzamide 
• 76570-56-4 Acetic acid 2-(tert-butoxycarbonyl-methyl-amino)-5-methyl-phenyl ester 
• 76570-55-3 Acetic acid 2-(tert-butoxycarbonyl-methyl-amino)-phenyl ester 
• 934812-46-1 N-Boc-N-methyl-O-diphenylcarbamoyl hydroxylamine 

Relevant academic research and scientific papers

Synthesis of N-Fmoc-O-(N′-boc-N′-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides

The synthesis of N-Fmoc-O-(N′-Boc-N′-methyl)- aminohomoserine in 35% overall yield from L-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemo-selectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.

Synthesis and Hydrolytic Stability of N- and O-Methyloxyamine Linkers for the Synthesis of GlycoconjugatesSynthesis and Hydrolytic Stability of N- and O-Methyloxyamine Linkers for the Synthesis of Glycoconjugates

A comparison of the merits of N- and O-methyloxyamines as linkers for carbohydrates is presented for the first time. In particular, optimized synthetic routes for each linker type are given, and the ease of glycan conjugation is described. The hydrolytic stabilities of the respective oxyamine glycoconjugates under a variety of different conditions are reported. This provides insight into the factors that influence hydrolysis rates, and sheds light on the acid-catalysed hydrolysis mechanism.

Development of a multifunctional neoglycoside auxiliary for applications in glycomics research

A novel, multifunctional, tetrazine-containing neoglycoside auxiliary has been synthesized in three steps and 28% overall yield. The oxyamine was conjugated with unprotected carbohydrates under aqueous conditions (pH = 4.7), with DMF as a cosolvent, to provide neoglycosides in yields ranging between 51% and 68%. This auxiliary displayed broad advantages in the isolation and purification of complex carbohydrate mixtures, compatibility during extension by glycosyltransferases, and direct conjugation to chemical probes. Furthermore, the auxiliary can be removed in 96% yield under acidic conditions (0.25% TFA in H2O) that leave glycosidic linkages intact. Thereby, the tetrazine-containing neoglycoside auxiliary can serve to facilitate future glycomics investigations.

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Design and Scalable Synthesis of N-Alkylhydroxylamine Reagents for the Direct Iron-Catalyzed Installation of Medicinally Relevant Amines**

Secondary and tertiary alkylamines are privileged substance classes that are often found in pharmaceuticals and other biologically active small molecules. Herein, we report their direct synthesis from alkenes through an aminative difunctionalization reaction enabled by iron catalysis. A family of ten novel hydroxylamine-derived aminating reagents were designed for the installation of several medicinally relevant amine groups, such as methylamine, morpholine and piperazine, through the aminochlorination of alkenes. The method has excellent functional group tolerance and a broad scope of alkenes was converted to the corresponding products, including several drug-like molecules. Besides aminochlorination, the installation of other functionalities through aminoazidation, aminohydroxylation and even intramolecular carboamination reactions, was demonstrated, further highlighting the broad potential of these new reagents for the discovery of novel amination reactions.

Phosphonodiamidate prodrugs of N-alkoxy analogs of a fosmidomycin surrogate as antimalarial and antitubercular agents

A series of N-alkoxy analogs of a L-leucine ethyl ester phosphonodiamidate prodrug of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. These compounds originate b

Double prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents

A series of eleven double prodrug derivatives of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. A pivaloyloxymethyl (POM) phosphonate prodrug modification was c

OXADIAZEPINONE DERIVATIVES AND THEIR USE IN THE TREATMENT OF HEPATITIS B INFECTIONS

Provided herein are compounds of formula (IA) and (III) useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.