98737-29-2

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is used as a key intermediate in the synthesis of HIV-1 protease inhibitors. Its chiral structure plays a vital role in the development of these inhibitors, which are essential in the treatment of HIV/AIDS.
Used in Medicinal Chemistry:
(2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is employed as a building block in the synthesis of (hydroxyethyl)urea peptidomimetics and arylsulfonamides with anti-HIV activity. These compounds have the potential to offer new therapeutic options for the treatment of HIV/AIDS.
Used in Enantiomer Synthesis:
As an enantiomerically pure compound, (2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is used in the synthesis of enantiomer S. Atazanavir intermediate, which is an important component in the production of Atazanavir, an antiretroviral medication used to treat HIV/AIDS.

InChI:InChI=1/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13-/m0/s1

Upstream product

• 6814-64-8 methylenedimethyl sulfurane 
• 72155-45-4 Boc-L-phenylalaninal 
• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 136630-87-0 (2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol 
• 68709-71-7 tert-butyl 4-bromo-3-oxo-1-phenylbutan-2-ylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 357604-38-7 [(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester 
• 326480-02-8 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane 
• 357604-39-8 (3S)-t-butyldimethylsilyloxy-(2R)-(t-butyloxycarbonyl)amino-4-chloro-1-phenylthiobutane 
• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 67-63-0 isopropyl alcohol 
• 77-92-9 citric acid 

Downstream Products

• 153864-55-2 (2S,3S)-3-(tert-butoxycarbonylamino)-4-phenyl-1-phenylthio-2-butanol 
• 162538-06-9 {(1S,2R)-1-Benzyl-3-[benzyl-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 162536-72-3 [R-(R*,S*)]-[3-Azido-2-hydroxy-1-(phenylmethyl) propyl]carbamic acid, 1,1-dimethylethyl ester 
• 162536-42-7 (1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 
• 264884-00-6 {(1S,2R)-1-Benzyl-3-[(2S,4R)-2-tert-butylcarbamoyl-4-(pyridin-4-ylsulfanyl)-piperidin-1-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 1054656-16-4 {(1S,2R)-1-Benzyl-3-[(2S,4R)-2-tert-butylcarbamoyl-4-(pyridin-4-ylmethylsulfanyl)-piperidin-1-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 189205-48-9 {(1S,2R)-1-Benzyl-3-[(2S,4R)-2-tert-butylcarbamoyl-4-(pyridin-3-ylmethylsulfanyl)-piperidin-1-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 154611-90-2 {(1S,2R)-1-Benzyl-3-[(2S,4R)-2-tert-butylcarbamoyl-4-(2,6-dimethyl-pyrimidin-4-ylsulfanyl)-piperidin-1-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 160232-23-5 tert-butyl (2S,3R)-3-hydroxy-4-(isopropyllamino)-1-phenylbutan-2-yl-carbamate 
• 251105-80-3 N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride 
• 388072-84-2 tert-butyl (2S,3R)-3-hydroxy-4-(ethylamino)-1-phenylbutan-2-yl-carbamate 
• 183553-44-8 tert-butyl (2S,3R)-4-(tert-butylamino)-3-hydroxy-1-phenylbutan-2-yl-carbamate 
• 338462-91-2 3-carbethoxy-5(R)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane

The invention relates to the technical field of synthesis of drug intermediates, in particular to a synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The method comprises the following steps: condensing N-t-butyloxycarboryl-L-phenylalanine serving as a raw material with substituted phenol under the action of a condensing agent to obtain active ester 15; reacting the active ester 15 with a ylide reagent and alkali to obtain a sulfoxide ylide intermediate 16; reacting the sulfoxide ylide intermediate 16 with halide salt under the action of a catalyst to obtain a halogenated ketone intermediate 6; reducing the halogenated ketone intermediate 6 through a reducing agent under the action of a catalyst to obtain a halogenated methanol intermediate 7; and removing halogen acid from the halogenated methanol intermediate 7 under the action of alkali, and carrying out condensation cyclization to obtain the target product (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The synthesis method of the (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane, provided by the invention, has the characteristics of cheap and easily available initial raw materials, safe and controllable process and easiness in operation.

Kinetic study on the reaction of p-tert-butylbenzoic acid with methanol catalyzed by deep eutectic solvent based on choline chloride

The synthesis of methyl p-tert-butylbenzoate using deep eutectic solvent (DES) as a green catalyst was studied in this work. Four DESs were prepared by combining choline chloride (ChCl) and p-toluenesulfonic acid monohydrate (PTSA) with different molar ratios (1:1–3). It was found that ChCl-1.5PTSA with a molar ratio of 1:1.5 was superior to other DESs both in physical properties and catalytic performance. Therefore, it was selected to carry out the kinetic experiments. The effects of stirring speed, temperature, molar ratio of methanol to p-tert-butylbenzoic acid, and catalyst loading on the conversion of p-tert-butylbenzoic acid were discussed. In addition, the reaction kinetics of p-tert-butylbenzoic acid and methanol with ChCl-1.5PTSA as catalyst was explored in the temperature range of 332.15–349.15 K, and the experimental data were well fitted by pseudo-homogeneous model. Moreover, the recyclability of ChCl-1.5PTSA was evaluated. The result shows that the catalyst could be easily separated from the reaction system without any extractant, and the performance of the catalyst remains stable in multiple times recycling. Therefore, ChCl-1.5PTSA is expected to be an efficient and environmentally friendly catalyst for the methyl esterification of p-tert-butylbenzoic acid with a bright future in industrial application.

Aerobic oxidative C?C bond cleavage of aromatic alkenes by a high valency iron-containing perovskite catalyst

High valency iron-containing perovskite catalyst BaFeO3-dcould efficiently promote the additive-free oxidative C?C bond cleavage of various aromatic alkenes to the corresponding aldehydes or ketones using O2as the sole oxidant. This system was applicable to the gram-scale oxidation of 1,1-diphenylethylene, in which 2.71 g (75% yield) of the analytically pure ketone could be isolated.

Combining photoredox catalysis and oxoammonium cations for the oxidation of aromatic alcohols to carboxylic acids

A methodology is reported for converting alcohols to the corresponding carboxylic acids. A dual catalytic system involving a merger of photoredox catalysis and 4-acetamido-TEMPO is employed to carry out this oxidation process.

Heterogeneous vanadium-catalyzed oxidative cleavage of olefins for sustainable synthesis of carboxylic acids

The development of green and sustainable processes to synthesize active pharmaceutical ingredients and key starting materials is a priority for the pharmaceutical industry. A green and sustainable protocol for the oxidative cleavage of olefins to produce pharmaceutically and biologically valuable carboxylic acids is achieved. The developed protocol involves 70% aq. TBHP as an oxidant over a heterogeneous vanadium catalyst system. Notably, the synthesis of industrially important azelaic acid from various renewable vegetable oils is accomplished. The catalyst could be recycled for up to 5 cycles without significant loss in yield and the protocol was successfully demonstrated at the gram-scale.

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Merging N-Hydroxyphthalimide into Metal-Organic Frameworks for Highly Efficient and Environmentally Benign Aerobic Oxidation

Two highly efficient metal-organic framework catalysts TJU-68-NHPI and TJU-68-NDHPI have been successfully synthesized through solvothermal reactions of which the frameworks are merged with N-hydroxyphthalimide (NHPI) units, resulting in the decoration of pore surfaces with highly active nitroxyl catalytic sites. When t-butyl nitrite (TBN) is used as co-catalyst, the as-synthesized MOFs are demonstrated to be highly efficient and recyclable catalysts for a novel three-phase heterogeneous oxidation of activated C?H bond of primary and secondary alcohols, and benzyl compounds under mild conditions. Based on the high efficiency and selectivity, an environmentally benign system with good sustainability, mild conditions, simple work-up procedure has been established for practical oxidation of a wide range of substrates.

An aerobic oxidation of alcohols into carbonyl synthons using bipyridyl-cinchona based palladium catalyst

We have reported an aerobic oxidation of primary and secondary alcohols to respective aldehydes and ketones using a bipyridyl-cinchona alkaloid based palladium catalytic system (PdAc-5) using oxygen at moderate pressure. ThePdAc-5catalyst was analysed using SEM, EDAX, and XPS analysis. The above catalytic system is used in experiments for different oxidation systems which include different solvents, additives, and bases which are cheap, robust, non-toxic, and commercially available on the industrial bench. The obtained products are quite appreciable in both yield and selectivity (70-85%). In addition, numerous important studies, such as comparisons with various commercial catalysts, solvent systems, mixture of solvents, and catalyst mole%, were conducted usingPdAc-5. The synthetic strategy of oxidation of alcohol into carbonyl compounds was well established and all the products were analysed using1H NMR,13CNMR and GC-mass analyses.

Continuous production method of benzoic acid derivative

The invention relates to the technical field of preparation of benzoic acid derivatives. The invention particularly relates to a continuous production method of a benzoic acid derivative. The continuous reaction device is characterized by comprising a small-diameter sleeve, wherein the small-diameter sleeve is sleeved with a large-diameter sleeve, and a small pipeline is arranged between the small-diameter sleeve and the large-diameter sleeve, and a plurality of small holes are arranged on the small pipeline. The small-diameter casing is rotated, the large-diameter casing is fixed, and the reaction liquid composed of the nitric acid and the toluene derivative is between a small-diameter casing pipe and a large-diameter casing pipe.

Photo-induced deep aerobic oxidation of alkyl aromatics

Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].