19790-60-4

Usage

Uses

Used in Pharmaceutical Industry:
3-BENZYLOXY-PROPIONALDEHYDE is used as a key intermediate for the chemoenzymatic synthesis of threoand erythro-β-hydroxy-L-glutamic acid derivatives. These derivatives are essential components in the development of pharmaceuticals, particularly those targeting various medical conditions and diseases. The compound's role in this synthesis process highlights its importance in the creation of potentially life-saving medications.

Upstream product

• 78314-63-3 3-benzyloxypropionaldehyde diethyl acetal 
• 88191-39-3 (Z)-((hex-3-en-1-yloxy)-methyl)benzene 
• 71998-69-1 (+/-)-4-benzyloxy-butane-1,2-diol 
• 143618-78-4 Oxo-phenyl-acetic acid 3-benzyloxy-propyl ester 
• 100-52-7 benzaldehyde 
• 504-63-2 trimethyleneglycol 
• 203738-77-6 3-tert-butyldimethylsilyloxy-1-propyl benzyl ether 
• 100-51-6 benzyl alcohol 
• 220061-73-4 2-(3-Benzyloxy-propoxy)-tetrahydro-pyran 
• 2134-29-4 3-Hydroxypropanal 
• 100-39-0 benzyl bromide 
• 4541-14-4 4-benzyloxy-butan-1-ol 
• 94426-71-8 (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 70388-33-9 4-benzyloxybut-1-ene 

Downstream Products

• 87413-14-7 (1S,5R,6R)-6-(2-Benzyloxy-ethyl)-4,5-dimethyl-2,7-dioxa-bicyclo[3.2.0]hept-3-ene 
• 106914-54-9 (3,3-Bis-tert-butylperoxy-propoxymethyl)-benzene 
• 119405-98-0 1,1-Dibromo-4-(phenylmethoxy)-1-butene 
• 116376-13-7 (4R^*,3R^*)-1-(benzyloxy)-4-methoxy-5-hexen-3-ol 
• 105346-31-4 5-(2-benzyloxyethyl)-3-hydroxy-4-phenyl-2(5H)-furanone 
• 111322-01-1 (R)-1-benzyloxy-hex-5-en-3-ol 
• 91285-62-0 (S)-1-(benzyloxy)-3-hydroxyhex-5-ene 
• 119046-50-3 (E)-5-Benzyloxy-1-trimethylsilanyl-pent-1-en-3-ol 
• 157220-39-8 (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 141401-30-1 4-(3-Benzyloxy-propylamino)-butyric acid methyl ester 
• 95338-10-6 (R)-1,3-pentanediol 1-benzyl ether 
• 95338-12-8 (S)-1,3-pentanediol 1-benzyl ether 
• 108560-42-5 4-Benzyloxy-2-methylamino-butyronitrile 
• 117661-29-7 5-(benzyloxy)pent-1-en-3-ol 

Relevant academic research and scientific papers

Chiral polypropionate subunit by a chemoenzymatic approach

Enzymatic desymmetrization of meso-4-methyl-3,5-syn-dioxolan- 1,3,5,7- tetrol was found to be highly enantioselective leading to both acetylated enantiomers with high enantiomeric excess.

Anionically induced domino reactions; synthesis of analogues of marine sesquiterpenes

An anionically induced domino reaction is the key step in the synthesis of the isotwistane skeleton. This precursor can be transformed into the marine sesquiterpene 2-isocyanopupukeanane or its structural analogues.

Asymmetric synthesis of D- and L-2-deoxy-4-thioriboses

Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L- diethyl tartrate and (-)-D-diethyl tartrate.

Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar

Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v

Synthesis of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs

Prodrugs are derivatives of drugs which gives parent drug or release drug when it breaks inside the body by the presence of suitable enzyme, and then exert desired pharmacological effect. For many years, prodrug strategy has been developed enormously to solve many unwanted drug properties. In drug discovery and development, prodrugs have well-known pharmacokinetic effects of pharmacologically nimble products. Almost 10% of drugs permitted whole world are classified as prodrugs, where the application of a prodrug method during initial stages of development is an emergent fashion. Phosphorodiamidates prodrugs are well known anticancer agents particularly against leucomia. To improve the selectivity of the chemotherapeutic agents and reduce systemic toxicity, I herein report different types of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs.

Pyrazole Agonist of the Apelin Receptor Improves Symptoms of Metabolic Syndrome in Mice

Apelin receptor agonism improves symptoms of metabolic syndrome. However, endogenous apelin peptides have short half-lives, making their utility as potential drugs limited. Previously, we had identified a novel pyrazole-based agonist scaffold. Systematic modification of this scaffold was performed to produce compounds with improved ADME properties. Compound 13 with favorable agonist potency (cAMPi EC50 = 162 nM), human liver microsome stability (T1/2 = 62 min), and pharmacokinetic profile in rodents was identified. The compound was tested in a mouse model of diet-induced obesity (DIO) and metabolic syndrome for efficacy. Treatment with 13 led to significant weight loss, hypophagia, improved glucose utilization, reduced liver steatosis, and improvement of disease-associated biomarkers. In conclusion, a small-molecule agonist of the apelin receptor has been identified that is suitable for in vivo investigation of the apelinergic system in DIO and perhaps other diseases where this receptor has been implicated to play a role.

GDC-9545 (Giredestrant): A Potent and Orally Bioavailable Selective Estrogen Receptor Antagonist and Degrader with an Exceptional Preclinical Profile for ER+ Breast Cancer

Breast cancer remains a leading cause of cancer death in women, representing a significant unmet medical need. Here, we disclose our discovery efforts culminating in a clinical candidate, 35 (GDC-9545 or giredestrant). 35 is an efficient and potent selective estrogen receptor degrader (SERD) and a full antagonist, which translates into better antiproliferation activity than known SERDs (1, 6, 7, and 9) across multiple cell lines. Fine-tuning the physiochemical properties enabled once daily oral dosing of 35 in preclinical species and humans. 35 exhibits low drug-drug interaction liability and demonstrates excellent in vitro and in vivo safety profiles. At low doses, 35 induces tumor regressions either as a single agent or in combination with a CDK4/6 inhibitor in an ESR1Y537S mutant PDX or a wild-type ERα tumor model. Currently, 35 is being evaluated in Phase III clinical trials.

CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF

The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate

Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.