161513-47-9

Usage

Uses

Used in the Detonation Nanodiamond Industry:
(S)-1-(TERT-BUTOXYCARBONYL)-2,3-OXIRANYLMETHYLAMINE is used as a functionalizing agent for detonation nanodiamonds to enhance their optical properties. The compound's reactivity allows it to form covalent bonds with the surface of nanodiamonds, introducing NH2 functional groups that can improve the optical characteristics of these materials, such as their luminescence or light absorption properties.
Used in the Polymer Industry:
In the synthesis of poly(ethylene glycol) (PEG) based block copolymers, (S)-1-(TERT-BUTOXYCARBONYL)-2,3-OXIRANYLMETHYLAMINE serves as a key intermediate. These block copolymers are further utilized in the preparation of micelles loaded with mRNA for intracellular mRNA delivery. The compound's unique structure enables the formation of well-defined copolymers with tailored properties, which are essential for the efficient encapsulation and delivery of mRNA in various applications, such as gene therapy and vaccine development.

InChI:InChI=1/C8H15NO3/c1-8(2,3)12-7(10)9-4-6-5-11-6/h6H,4-5H2,1-3H3,(H,9,10)/t6-/m0/s1

Upstream product

• 148983-26-0 (S)-1-<(tert-butoxycarbonyl)amino>-2-hydroxy-3-<<(4-methylphenyl)sulfonyl>oxy>propane 
• 415684-05-8 tert-butyl (2S)-3-chloro-2-hydroxypropylcarbamate 
• 148982-76-7 tert-butyl N-(2-oxiranylmethyl)carbamate 
• 148983-25-9 (S)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 148983-23-7 (R)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 

Downstream Products

• 1416129-92-4 tert-butyl {(5S)-3-[4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methylcarbamate 
• 1082937-32-3 [(S)-3-(4-cyanophenyl)-2-oxo-oxazolidin-5-ylmethyl]-carbamic acid tert-butyl ester 
• 1429333-95-8 tert-butyl N-[(R)-2-hydroxy-3-{4-(3-oxomorpholin-4-yl)phenylamino}propyl]carbamate 
• 1112969-11-5 C₂₀H₂₃F₂N₃O₅ 
• 1112969-02-4 C₂₀H₂₂F₃N₃O₅ 
• 1082937-30-1 [(R)-3-(4-cyanophenylamino)-2-hydroxy-propyl]carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

BH4 ANTAGONISTS AND METHODS RELATED THERETO

The disclosure relates to BH4 inhibitors and therapeutic uses relates thereto. In certain embodiments, the disclosure relates to methods of treating or preventing cancer, such as lung cancer, comprising administering therapeutically effective amount of a pharmaceutical composition comprising a compound disclosed herein or pharmaceutically acceptable salt to a subject in need thereof.

NEW CHIRAL SALEN CATALYSTS AND METHODS FOR THE PREPARATION OF CHIRAL COMPOUNDS FROM RACEMIC EPOXIDES BY USING THEM

The present invention relates to new chiral salen catalysts and the preparation method of chiral compounds from racemic epoxides using the same. More specifically, it relates to new chiral salen catalysts that have high catalytic activity due to new molecular structures and have no or little racemization of the generated target chiral compounds even after the reaction is completed and can be also reused without catalyst regeneration treatment, and its economical preparation method to mass manufacture chiral compounds of high optical purity, which can be used as raw materials for chiral food additives, chiral drugs, or chiral crop protection agents, etc., using the new chiral salen catalysts.

PROCESS FOR PREPARATION OF OPTICALLY ACTIVE 1-SUBSTITUTED AMINO-2,3-EPOXYPROPANES, INTERMEDIATES FOR THE SYNTHESIS THEREOF AND PROCESS FOR PREPARATION OF THE INTERMEDIATES

The present invention provides an industrial process for effectively and advantageously preparing optically active 1-substituted amino-2,3-epoxypropanes useful as intermediates for preparing agricultural chemicals and medical products from optically activ

Esterolytic peptide dendrimers with a hydrophobic core and catalytic residues at the surface

(3S)-4-(9-Fluorenylmethoxycarbonylamino)-3-methyl(allyloxycarbonyl) aminoethyloxyacetic acid (1) was prepared from (R)-3-aminopropane-1,2-diol and used as branching unit for the synthesis of second generation peptide dendrimers with six individually addressable variable amino acid positions. Three pairs of diastereomeric dendrimers were prepared bearing a common hydrophobic core and permutations of the catalytic triad amino acids aspartate, histidine and serine at the surface. Dendrimers with two surface histidine residues catalyzed the hydrolysis of fluorogenic 8-acyloxypyrene-1,3,6-trisulfonates in aqueous buffer pH 6.0 with rate enhancement kcat/kuncat in the 10 3 range and Michaelis-Menten constants KM in the 10 -4 M range. Substrate recognition involves electrostatic interactions, as shown by competitive inhibition of catalysis observed with pyrene-1,3,6,8-tetrasulfonate. The 4-fold to 7-fold lowering in KM between the butyryl and nonanoyl esters in the most active dendrimers provides evidence for a hydrophobic component in substrate binding, which is absent in a closely related, less active diastereomeric peptide dendrimer.

The synthesis of N-aryl-5(S)-aminomethyl-2-oxazolidinone antibacterials and derivatives in one step from aryl carbamates

Since 1993, a significant process research and development effort directed towards the large-scale synthesis of oxazolidinone antibacterial agents has been ongoing in both Early Chemical Process Research and Development, and Chemical Process Research and Development at Pharmacia. This work has led to the successful development of the current commercial process to produce Zyvox (linezolid), recently approved by the FDA as an antibacterial. While this synthesis is appropriate for the preparation of linezolid in particular, a more convergent and versatile synthesis was developed for the rapid preparation of numerous other oxazolidinone analogues. Toward this end, economical methods for the large-scale preparation of N-[(2S)-2-(acetyloxy)-3-chloropropyl]acetamide 3 and tert-butyl [(2S)-3-chloro-2-hydroxypropyl]carbamate 27 from commercially available (S)-epichlorohydrin via the common intermediate (2S)-1-amino-3-chloro-2-propanol hydrochloride 2a were developed. Also, general methods for coupling these reagents with N-aryl carbamates to give N-aryl-5(S)-aminomethyl-2-oxazolidinone derivatives in one step were developed. These reagents and procedures have proven widely applicable in the preparation of a diverse array of oxazolidinone analogues such as 23 and 28 in both process and medicinal chemistry research.

Methods of producing oxazolidinone compounds

Methods of synthesizing pharmacologically useful oxazolidinones are disclosed, and, in particular, a method of manufacturing a 5-(tert-butylcarbamoyl)-aminomethyl-oxazolidinone by condensing a carbamate with a tert-butylcarbamoyl protected derivative of g

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.

Synthesis and Structure-Activity Relationships of a Series of Penicillin-Derived HIV Proteinase Inhibitors: Heterocyclic Ring Systems Containing P'1 and P'2 Substituents

As an extension of our earlier work based upon a single penicillin-derived thiazolidine moiety we have found that the decahydroisoquinoline grouping, also present in Ro 31-8959, is an effective replacement for one of the thiazolidine units in C2 symmetric penicillin-derived dimers.Reaction of racemic epoxide 6 with -decahydro-N-(1,1-dimethylethyl)-3-isoquinolinecarboxamide gave diastereoisomers 34a and 34b.The stereochemistry of the hydroxyl grouping of 34a was determined to be (S).Reaction of the amines derived from 34a and 34b with thiazolidine 8a gave 50 and 51, respectively.Compound 50 was a potent inhibitor of HIV proteinase (IC50 = 23 nM) with antiviral activity against HIV-1 in vitro (EC50 C8166 cells = 50 nM).However, a poor pharmacokinetic profile in the dog for compound 50 and its analogues, in keeping with earlier studies on penicillin-derived dimers in three species, precluded their development as potential antivirals.