149057-20-5

Basic information

• Product Name: Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI);(R)-N-Boc-2,3-epoxypropylamine;(R)-tert-Butyl (oxiran-2-ylMethyl)carbaMate;(R)-1-(t-Butoxycarbonyl)-2,3-oxiranylaMine
• CAS NO: 149057-20-5
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.2096
• Product Categories: N-BOC
• Mol File: 149057-20-5.mol

Chemical Properties

• Melting Point: 76-77 °C
• Boiling Point: 262.908°C at 760 mmHg
• Flash Point: 112.803°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.462
• PKA: 12.45±0.46(Predicted)
• CAS DataBase Reference: Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI)(149057-20-5)
• EPA Substance Registry System: Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI)(149057-20-5)

Safety Data

• Hazardous Substances Data: 149057-20-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI) is used as a key intermediate in organic synthesis for the creation of various organic compounds. Its unique structure, including the t-butyl ester group and oxirane ring, allows for a broad range of chemical reactions, facilitating the synthesis of complex molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI) is utilized as a reagent in the development of new drugs. Its ability to participate in numerous chemical reactions makes it an essential component in the synthesis of potential therapeutic agents, contributing to the advancement of medicinal chemistry.
Used in Research and Development:
Carbamic acid, [(2R)-oxiranylmethyl]-, 1,1-dimethylethyl ester (9CI) is employed as a research tool in academic and industrial laboratories. Its versatility in organic synthesis and potential applications in pharmaceuticals make it a valuable compound for exploring new chemical pathways and discovering novel molecular structures.

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-/m1/s1

Upstream product

• 148983-23-7 (R)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 148982-76-7 tert-butyl N-(2-oxiranylmethyl)carbamate 
• 1072792-33-6 (R)-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 148983-24-8 (R)-1-<(tert-butoxycarbonyl)amino>-2-hydroxy-3-<<(4-methylphenyl)sulfonyl>oxy>propane 
• 34619-03-9 tert-butyldicarbonate 
• 570390-94-2 tert-butyl-3-chloro-2-hydroxypropylcarbamate 
• 137618-48-5 tert-butyl N-(2,3-dihydroxypropyl)carbamate 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 

Downstream Products

• 148983-25-9 (S)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 148983-23-7 (R)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 161513-47-9 (S)-<<(tert-butoxycarbonyl)amino>methyl>oxirane 
• 144912-84-5 (3-amino-2-hydroxypropyl)carbamic acid 1,1-dimethylethyl ester 
• 853944-08-8 (2S)-N-tert-butoxycarbonyl-2-hydroxy-1,3-diaminopropane 
• 1072828-18-2 [(R)-3-(3-fluoro-4-methyl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-carbamic acid tert-butyl ester 
• 1303996-67-9 C₁₇H₃₄N₂O₁₁ 

Relevant articles and documents

Coupling of CO2and epoxides catalysed by novel: N-fused mesoionic carbene complexes of nickel(ii)

We report the syntheses of two rigid mesoionic carbene (MIC) ligands with a carbazole backbone via an intramolecular Finkelstein-cyclisation cascade and investigate their coordination behavior towards nickel(ii) acetate. Despite the nickel(ii) carbene complexes 4a,b showing only minor differences in their chemical composition, they display curious differences in their chemical properties, e.g. solubility. Furthermore, the potential of these novel MIC complexes in the coupling of carbon dioxide and epoxides as well as the differences in reactivity compared to classical NHC-derived complexes are evaluated.

BISPHOSPHONATE-LINKED COMPOUNDS

The present invention concerns novel compounds useful in the treatment of cancer, particularly including compounds linking a bisphosphonate moiety with KBU2046, and pharmaceutically acceptable salts, co-crystals, polymorphs, solvates, hydrates, and enantiomers thereof, as well as methods for their production and pharmaceutical compositions comprising them.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

TGR5 AGONISTS

The invention relates to novel 1,4-diazepan-2-one compounds, which are TGR5 agonists and useful for the treatment of metabolic disorders, inflammatory diseases, atherosclerosis and dyslipidemias.

Novel synthesis of fluorochrome-coupled zoledronate with preserved functional activity on gamma/delta T cells and tumor cells

In addition to their effects on bone resorption, nitrogen-containing bisphosphonates (N-BP) selectively activate γδ T cells, an innate-like immune cell population with potent anti-tumor activity. N-BP stimulate γδ T cells through induction of intracellular accumulation of mevalonate pathway-derived pyrophosphates, which are strong and selective antigens for human γδ T cells. The most potent among several classes of N-BP is zoledronate (ZOL). To study the uptake of ZOL and its immunological consequences in the γδ T cell/tumor cell interplay, we have synthesized a novel fluorescently labeled ZOL derivative termed FluorZOL by covalently coupling ZOL to carboxyfluorescein succinidimyl ester. Here we describe in detail the synthesis of FluorZOL and we further show that FluorZOL is functionally fully active as revealed by the selective expansion of γδ T cells and the enhancement of tumor cell lysis by γδ T cells.

Novel fluorescent risedronates: Synthesis, photodynamic inactivation and imaging of Bacillus subtilis

Novel fluorescently-labeled conjugates of risedronate were synthesized using an epoxide linker, enabling conjugation of risedronate via its pyridyl nitrogen with the aromatic succinimidyl esters. The compounds were characterized by using 1H NMR, 13C NMR, 31P NMR, UV-vis and fluorescence emission spectroscopies. Biological activity assays showed that the conjugates 14 and 15 exhibited photodynamic inactivation of Bacillus subtilis (ATCC 6633) with 91% and 47% bacterial lethality at 10 μM upon visible light irradiation, respectively. Both 14 and 15 could be also used for fluorescence imaging of Bacillus subtilis.

Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines

Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.

Highly regioselective and efficient synthesis of aminoepoxides by ring closure of aminohalohydrins mediated by KF-Celite

The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed. Georg Thieme Verlag Stuttgart . New York.

Selective delivery of 2-hydroxy APA to Trypanosoma brucei using the melamine motif

Trypanosoma brucei, the parasite that causes human African trypanosomiasis, is auxotrophic for purines and has specialist nucleoside transporters to import these metabolites. In particular, the P2 aminopurine transporter can also selectively accumulate melamine derivatives. In this Letter, we report the coupling of the melamine moiety to 2-hydroxy APA, a potent ornithine decarboxylase inhibitor, with the aim of selectively delivering this compound to the parasite. The best compound described here shows an increased in vitro trypanocidal activity compared with the parent.

OXAZOLIDINONE ANTIBIOTIC DERIVATIVES

The invention relates to antibacterial compounds of formula I wherein R1 is hydrogen, halogen, hydroxy, alkoxy or cyano; Y1 and Y2 each represent CH, one or two of U, V, W and X represent(s) N and the remaining each represent CH or, in the case of X, may also represent CRa, Ra being halogen, and, in the case of W, may also represent CRb, or each of U, V, W, X, Y1 and Y2 represents CH, or each of U, V, W, X and Y1 represents CH and Y2 represents N, or also one or, provided R1 is hydrogen, two of U, V, W, X, Y1 and Y2 represent(s) CRC and the remaining each represent CH, Rb being alkoxy, alkoxycarbonyl or alkoxyalkoxy and Rc being, each time it occurs, independently represents hydroxy or alkoxy; A-B-D represents a chain of 4 to 6 atoms, which 4 to 6 atoms are seleted from carbon, oxygen and nitrogen and may be substituted; E is one of the following groups: in which Z is CH or N and Q is O or S, or E is a phenyl group which is substituted once or twice in the meta and/or para position(s); and to salts of such compounds.