158690-56-3

Basic information

• Product Name: TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE
• Synonyms: TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE;2-([[(1,1-Dimethylethyl)oxy]carbonyl]amino)ethyl 4-methylbenzenesulfonate;2-(tert-butoxycarbonylaMino)ethyl 4-Methylbenzenesulfonate;2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 4-methylbenzenesulfonate;Tert-Butyl N-[2-(Tos
• CAS NO: 158690-56-3
• Molecular Formula: C₁₄H₂₁NO₅S
• Molecular Weight: 315.39
• Mol File: 158690-56-3.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 461.949 °C at 760 mmHg
• Flash Point: 233.179 °C
• Appearance: /
• Density: 1.189±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C(protect from light)
• PKA: 11.71±0.46(Predicted)
• CAS DataBase Reference: TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE(158690-56-3)
• EPA Substance Registry System: TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE(158690-56-3)

Safety Data

• Hazardous Substances Data: 158690-56-3(Hazardous Substances Data)

Usage

General Description

Tert-butyl N-[2-(tosyloxy)ethyl]carbamate is a chemical compound that is commonly used in organic synthesis and chemical reactions. It is a carbamate derivative, with the tert-butyl group as a protecting group for a primary amine and the tosyl group as a good leaving group for substitution reactions. TERT-BUTYL N-[2-(TOSYLOXY)ETHYL]CARBAMATE is frequently employed as a reagent in the process of protecting primary amines in chemical synthesis, allowing for selective reaction at other functional groups while keeping the amine group unreactive. It is also used in the production of pharmaceuticals and agrochemicals, as well as in the development of various other organic compounds. Overall, tert-butyl N-[2-(tosyloxy)ethyl]carbamate plays a crucial role in the field of organic chemistry and is widely utilized in the synthesis of various complex molecules.

InChI:InChI=1/C14H21NO5S/c1-11-5-7-12(8-6-11)21(17,18)19-10-9-15-13(16)20-14(2,3)4/h5-8H,9-10H2,1-4H3,(H,15,16)

Upstream product

• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 497-25-6 dimethylenecyclourethane 
• 873330-01-9 N-boc-2-benzylsulfanyl-ethylamine 
• 919286-21-8 tert-butyl (2-(4-(trifluoromethyl)phenoxy)ethyl)carbamate 
• 1593201-17-2 4-(2-(tert-butyloxycarbonylamino)ethoxy)phenyl bromide 
• 1204333-53-8 C₁₃H₁₈BrNO₃ 
• 252263-98-2 3-[2-(tert-butoxycarbonylamino)ethoxy]benzonitrile 
• 246240-09-5 tert-butyl (2-(3-nitrophenoxy)ethyl)carbamate 
• 1329611-57-5 C₁₄H₂₁NO₄ 
• 1098107-26-6 N-(2-(3-bromophenoxy)ethyl)carbamic acid tert-butyl ester 

Relevant articles and documents

C-terminal 18F-fluoroethylamidation exemplified on [Gly-OH9] oxytocin

The no-carrier-added (n.c.a.) 18F-fluoroethylamidation of the acid function of the protected nonapeptide Boc-Cys-Tyr(tBu)-Ile-Gln(Mtt)-Asn(Mtt)-Cys-Pro-Leu-Gly-OH forming the labelled peptide hormone derivative [Gly-(2-[18F]fluoroeth

High Stability of a Donor-Acceptor Type Oxazepine-Containing Fluorophore and Its Applications in Cellular Imaging and Two-Photon Deep Tissue Imaging

A new donor (D)-acceptor (A) type naphthalene-based oxazepine-containing fluorophore, OXN-1, is reported, which shows unusually high stability in various environments. Its photophysical properties and structural stabilities under harsh conditions are thor

Design and Synthesis of New 9-Substituted Norharmane Derivatives as Potential Sirt5 Inhibitors

Sirt5 is a potential new drug target for the treatment of cancer, Alzheimer's disease, and Parkinson's disease. Given that norharmane is an important chemical synthon for some biologically important compounds and 9-substituted norharmane derivatives containing a negatively charged carboxyl group may accord with the characteristic of potential Sirt5 inhibitors, a series of novel 9-substituted norharmane derivatives were synthesized. The chemical structures and purities of all the target compounds were characterized by 1H NMR, 13C NMR, MS, and HPLC. By in vitro SIRT5 inhibitory assays, three compounds (1a, 3a, and 3b) show over 30% inhibition ratios at concentration of 100 μM, and the most active compound 3b has 35% and 52% inhibition ratios at 30 μM and 100 μM, respectively. Docking analysis showed that compound 3b is likely to fit very well on the substrate binding site of Sirt5, and hence, we believe that compound 3b can serve as a lead compound for further efforts to develop specific Sirt5 inhibitors.

Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter

Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.

Efficient Targeted Degradation via Reversible and Irreversible Covalent PROTACs

Proteolysis targeting chimeras (PROTACs) represent an exciting inhibitory modality with many advantages, including substoichiometric degradation of targets. Their scope, though, is still limited to date by the requirement for a sufficiently potent target binder. A solution that proved useful in tackling challenging targets is the use of electrophiles to allow irreversible binding to the target. However, such binding will negate the catalytic nature of PROTACs. Reversible covalent PROTACs potentially offer the best of both worlds. They possess the potency and selectivity associated with the formation of the covalent bond, while being able to dissociate and regenerate once the protein target is degraded. Using Bruton's tyrosine kinase (BTK) as a clinically relevant model system, we show efficient degradation by noncovalent, irreversible covalent, and reversible covalent PROTACs, with 85% degradation. Our data suggest that part of the degradation by our irreversible covalent PROTACs is driven by reversible binding prior to covalent bond formation, while the reversible covalent PROTACs drive degradation primarily by covalent engagement. The PROTACs showed enhanced inhibition of B cell activation compared to ibrutinib and exhibit potent degradation of BTK in patient-derived primary chronic lymphocytic leukemia cells. The most potent reversible covalent PROTAC, RC-3, exhibited enhanced selectivity toward BTK compared to noncovalent and irreversible covalent PROTACs. These compounds may pave the way for the design of covalent PROTACs for a wide variety of challenging targets.