79413-93-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-BROMO-1,2-EPOXYBUTANE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature allows for the production of enantiomerically pure drugs, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-4-BROMO-1,2-EPOXYBUTANE is utilized as a precursor for the development of chiral pesticides and other agrochemicals. Its unique spatial arrangement of atoms enables the creation of more effective and targeted pest control solutions.
Used in Organic Synthesis:
(R)-4-BROMO-1,2-EPOXYBUTANE is employed as a reagent in various organic synthesis reactions, including ring-opening reactions, nucleophilic substitutions, and other transformations. Its versatility and reactivity make it a valuable tool in the synthesis of complex organic molecules.
Safety Precautions:
Due to its toxic nature and potential to cause allergic skin reactions, it is essential to handle (R)-4-BROMO-1,2-EPOXYBUTANE with care. It should only be used in a well-ventilated area and with proper protective equipment, such as gloves, goggles, and a lab coat, to minimize exposure risks.

Upstream product

• 70681-41-3 (R)-dimethyl malate 
• 64028-90-6 (S)-1,4-dibromo-2-butanol 
• 13287-42-8 (2-bromoethyl)oxirane 

Downstream Products

• 674483-18-2 (R)-8-acenaphthen-1-yl-1-(4-fluorophenyl)-3-(2-(R)-oxiranyl-ethyl)-1,3,8-triazaspiro[4.5]decan-4-one 
• 794466-70-9 (3R)-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl}pyrrolidin-3-ol 

Relevant academic research and scientific papers

Predictable stereoselective and chemoselective hydroxylations and epoxidations with P450 3A4

Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

Enantiomerically Pure Synthetic Building Blocks with Four C-Atoms and Two or Three Functional Groups from β-Hydroxy-butanoic, Malic, and Tartaric Acid

The pool of chiral, non-racemic electrophilic building blocks, which are available from simple natural products in both enantiomeric forms is enlarged by the epoxides 3, 5, and 10, by the tosylate 12a, and by the aldehydes 18 (cf. symbols A-D, 14, and Scheme 1).Key steps of the conversions leading from hydroxyacids to the building blocks are: epoxide-opening by triethylborohydride (1 --> 2a) and tosylate reduction (12a --> 12b); the Mitsunobu inversion (2a --> 4a); the reduction of (R,R)-tartaric ester to (R)-malic ester by NBS (N-bromosuccinimide) opening of the benzaldehyde acetal 8 and tin hydride reduction (6c -->7c); the enantiomer enrichment of optically active ethyl β-hydroxy-butanoate through the crystalline dinitrobenzoate 21b.Detailed procedures are given for large scale preparations of the key intermediates.The enantiomeric purities of the building blocks are secured by correlations.