54555-84-9

Usage

Uses

Used in Organic Synthesis:
1-Benzyloxy-2-Iodoethane is utilized as a reagent in organic synthesis for its ability to participate in various chemical reactions. Its unique structure, with an iodine atom and a benzyloxy group, makes it a valuable component in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Benzyloxy-2-Iodoethane is used as a building block for the development of new drugs. Its reactivity and functional groups allow chemists to create diverse medicinal compounds with potential therapeutic applications.
Used in Chemical Research:
1-Benzyloxy-2-Iodoethane is also employed in chemical research as a model compound to study the properties and reactions of alkyl halides. This helps researchers understand the behavior of similar compounds and develop new synthetic methods or applications.

Upstream product

• 624-76-0 Iodoethanol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 622-08-2 2-Benzyloxyethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1462-37-9 bromoethyl-2-benzyl ether 
• 17229-17-3 benzyl 2-chloroethyl ether 

Downstream Products

• 141764-65-0 Diethyl 5-Benzyloxy-2-oxopentylphosphonate 
• 140840-64-8 8-(2-Benzyloxy-ethyl)-7-(1H-indol-3-yl)-1,4-dioxa-8-aza-spiro[4.5]decane 
• 140840-63-7 7-(1-Benzenesulfonyl-1H-indol-3-yl)-8-(2-benzyloxy-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane 
• 134706-59-5 methyl (+/-)-3-<4-<2-(benzyloxy)ethyl>-4,5,6,7-tetrahydropyrazolo<1,5-a>pyridin-3-yl>-3-oxopropionate 
• 141938-74-1 4-((3S,4R)-1-Benzyl-3-ethyl-piperidin-4-yl)-2-(2-benzyloxy-ethyl)-3-oxo-butyric acid methyl ester 
• 141062-32-0 (S)-5-Benzyloxy-2-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-3-methyl-pentanoic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester 
• 10378-08-2 ethyl 6-(benzyloxy)-3-oxohexanoate 
• 113522-59-1 CH(CH₂CH₂OBn)(CO₂Me)2 
• 935-04-6 benzyl vinyl ether 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 134167-07-0 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-methoxypropanoate 
• 134167-08-1 Methyl N-Boc-N-(2-benzyloxyethyl)-2-aminoacrylate 
• 134167-06-9 methyl (2S)-3-(2-benzyloxyethoxy)-2-(tert-butoxycarbonylamino)propanoate 
• 1028302-49-9 4-Benzyloxy-2-[2-(2-methoxy-ethoxymethoxy)-benzoyl]-butyric acid ethyl ester 

Relevant academic research and scientific papers

MODULATORS OF G-PROTEIN COUPLED RECEPTORS

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt and/or hydrate and/or prodrug of the compound) that modulate (e.g., agonize or partially agonize or antagonize) glucagon?like peptide?1 receptor ("GLP?1R") and/or the gastric inhibitory polypeptide receptor ("GIPR"). The chemical entities are useful, e.g., for treating a subject (e.g., a human) having a disease, disorder, or condition in which modulation (e.g., agonism, partial agonism or antagonism) of GLP?1R and/or GIPR activities is benficial for the treatment or prevention of the underlying pathology and/or symptoms and/or progression of the disease, disorder, or condition. In some embodiments, the modulation results in an enhancment of (e.g., an increase in) existing levels (e.g., normal or below normal levels) of GLP?1R and/or GIPR activity (e.g., signaling). In some embodiments, the chemical entities described herein further modulate (e.g., attenuate, uncouple) -arrestin signaling relative to what is observed with the native ligand. This disclosure also features compositions as well as other methods of using and making the said chemical entities.

Domino Pd0-Catalyzed C(sp3)–H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates

The Pd0-catalyzed C(sp3)-H arylation of 2-bromo-N-methylanilides leads to unstable benzazetidine intermediates that rearrange to benzoxazines through 4π electrocyclic ring-opening and 6π electrocyclization. The introduction of a bulky, non-activatable amide group on the nitrogen atom was key to favor the challenging reductive elimination step and disfavor undesired reaction pathways.

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene

2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp2)-H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.

Palladium-catalyzed alkylation of ortho-C(sp2)-H bonds of benzylamide substrates with alkyl halides

A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of β-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.

Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.

ARYLOXY AND ARYLALKYLENEOXY SUBSTITUTED THIAZOLOQUINOLINES AND THIAZOLONAPHTHYRIDINES

Thiazoloquinoline and thiazolonaphthyridine compounds having an aryloxy or arylalkyleneoxy substituent at the 6-, 7-, 8-, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these

Highly efficient two-step synthesis of C-sp3-centered geminal diiodides

(Chemical Equation Presented) Trisubstituted gem-diiodoalkenes of functionalized chains are efficiently reduced to the corresponding terminal geminal diiodides in high yields upon treatment with the diazene precursor, diethyl 4-(hydrazinosulfonyl)-benzyl phosphonate.

Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide

Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright

Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells

A class of structurally simplified analogues of the naturally occurring annonaceous acetogenins were developed, amongst which some non-THF analogues showed remarkable cytotoxicities against tumor cell lines, as well as good selectivity between human tumor cells and normal cells. The synthetic routes were significantly shortened because of the removal of the chiral centers bearing the THF rings on the natural templates. This simplification also provides access to the parallel synthesis of these mimics by a combinatorial strategy. The remaining stereogenic centers at the positions α to the ethereal links were introduced by the Chiron approach from the easily accessible chiral building blocks 6a and/or 6b, made in turn from L-ascorbic acid or Dmannitol, while the one in the butenolide segment was taken from L-lactate. All four diastereomeric non-THF analogues 2a-2d showed remarkable activity against the HCT-8 cell line, and better differentiation was found when testing against the HT-29 cell line. It was also discovered that both the butenolide and ethylene glycol subunits play essential roles in the cytotoxicities against tumor cell lines, while the 10-substituted hydroxy group and the absolute configuration of methyl group at the butenolide moiety are less important for their activity.