124988-64-3

Upstream product

• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 134916-70-4 4-phenylbutane-1,2-diyl diacetate 
• 2243-53-0 trans-styrylacetic acid 
• 122-78-1 phenylacetaldehyde 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 1192826-26-8 4-phenethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 768-56-9 4-Phenylbut-1-ene 
• 124888-60-4 4-phenylbutane-1,2-diol 
• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 
• 6921-34-2 benzylmagnesium chloride 
• 152978-83-1 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-4-phenyl-3-butenoate 
• 153062-67-0 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-2-diazo-4-phenyl-3-butenoate 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 19969-15-4 4-Phenyl-butan-diol-(1,2)-bis-phenyl-urethan 
• 173917-44-7 1-(tert-butyl-dimethylsilyloxy)-4-phenylbutan-2-ol 
• 1192826-26-8 4-phenethyl-1,3-dioxolane 
• 1189195-95-6 C₁₂H₁₅NO₅S 
• 501-52-0 3-Phenylpropionic acid 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 1567840-67-8 2,2-di-tert-butyl-4-phenethyl-1,3,2-dioxasilolane 
• 710-11-2 2-oxo-4-phenylbutyric acid 
• 143216-63-1 (2R,4R)-4-Amino-4-phenyl-butane-1,2-diol 
• 212560-65-1 (R)-tert-butyl (3-oxo-1-phenylpropyl)carbamate 
• 620989-96-0 (2R,4S)-4-Amino-4-phenyl-butane-1,2-diol 
• 118629-73-5 (S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 
• 851372-04-8 (2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 
• 1161878-62-1 (S)-1,2-dimethoxy-4-phenylbutane 

Relevant academic research and scientific papers

Enantioselective reduction of α-keto esters to 1,2-diols using the NaBH4/Me3SiCl system catalyzed by polymer-supported chiral sulfonamide

In the presence of 25mol% of a polymer-supported chiral sulfonamide, a variety of α-keto esters can be reduced into the corresponding 1,2-diols in good yields and high enantioselectivities using the NaBH4/Me 3SiCl reducing system.

Microencapsulated Osmium Tetroxide-Catalyzed Asymmetric Dihydroxylation of Olefins in Water without Using Organic Cosolvents

The asymmetric dihydroxylation of olefin using phenoxyethoxymethyl- polystyrene (PEM)-based microencapsulated osmium tetroxide (PEM-MC OsO 4) proceeded smoothly in water as the sole solvent. The catalyst was recovered quantitatively by simple filtration and reused several times without loss of activity.

Lewis Base Catalyzed Dioxygenation of Olefins with Hypervalent Iodine Reagents

1,2-Diols are extremely useful building blocks in organic synthesis. Hypervalent iodine reagents are useful for the vicinal dihydroxylation of olefins to give 1,2-diols under metal-free conditions, but strongly acidic promoters are often required. Herein, we report a catalytic vicinal dioxygenation of olefins with hypervalent iodine reagents using Lewis bases as catalysts. The conditions are mild and compatible with various functional groups.

Concise, scalable and enantioselective total synthesis of prostaglandins

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Iron-Catalyzed Diborylation of Unactivated Aliphatic gem-Dihalogenoalkenes: Synthesis of 1,2-Bis(boryl)alkanes

Herein, we report the first example of iron-catalyzed defluoroborylation of unactivated gem-difluoroalkenes, gem-dichloroalkenes, and gem-dibromoalkenes, providing the 1,2-bis(boryl)alkanes in moderate to good yield. This transformation has high regiosele

Palladium-Catalyzed meta-C-H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including 1H NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.

Site-Selective Mono-Oxidation of 1,2-Bis(boronates)

Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Replacement of the Benzylpiperidine Moiety with Fluorinated Phenylalkyl Side Chains for the Development of GluN2B Receptor Ligands

The 4-benzylpiperidine moiety is a central structural element of potent N-methyl-d-aspartate (NMDA) receptor antagonists containing the GluN2B subunit. To obtain novel GluN2B ligands suitable for positron emission tomography, the benzylpiperidine moiety was replaced with fluorinated ω-phenylalkylamino groups. For this purpose three primary propyl- and butylamines 7 a–c and one butyraldehyde 7 d bearing a fluorine atom and an ω-phenyl moiety were prepared in 3- to 7-step syntheses. Compounds 7 a–d were attached to various scaffolds of potent GluN2B antagonists (scaffold hopping) instead of the original 4-benzylpiperidine moiety. Although benzoxazol-2-ones and indoles with a benzylpiperidine moiety show high GluN2B affinity, the corresponding fluorophenylalkylamine derivatives did not result in high Glu2B affinity. Moderate GluN2B affinity was observed for a 3-(fluoroalkyl)-substituted tetrahydro-1H-3-benzazepine (Ki=239 nm). However, high GluN2B affinity was obtained for the tetrahydro-5H-benzo[7]annulen-7-amines 12 a–c (Ki=17–30 nm). Docking studies resulted in the same binding pose for 12 a as for the lead compound Ro 25-6981. It can be concluded that some GluN2B ligands (benzoxazolones, indoles) do not tolerate replacement of the 4-benzylpiperidine moiety with flexible fluorinated phenylalkyl side chains, but other scaffolds such as tetrahydro-3-benzazepines and -benzo[7]annulenes retain interaction with NMDA receptors containing the GluN2B subunit.