52657-84-8

Upstream product

• 623-70-1 ethyl (E)-crotonate 
• 100-51-6 benzyl alcohol 
• 371252-43-6 3-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)oxy butane 
• 100-99-2 triisobutylaluminum 
• 774-44-7 (±)-(2S,4R)-2,4-dimethyl-1,3-dioxane 
• 774-44-7 4-methyl-2-phenyl-[1,3]dioxane 
• 92156-52-0 ethyl 3-[(phenylmethyl)oxy]butanoate 
• 100-52-7 benzaldehyde 
• 18826-95-4 1.3-butanediol 
• 100-39-0 benzyl bromide 

Downstream Products

• 90812-70-7 3-benzyloxy-1-iodobutane 
• 90458-77-8 3-(benzyloxy)butanal 
• 671232-61-4 (E)-5-Benzyloxy-hex-2-en-1-ol 
• 671232-62-5 [(2S,3S)-3-(2-Benzyloxy-propyl)-oxiranyl]-methanol 
• 370863-15-3 7-benzyloxy-4-oxo-2-octenal 
• 370863-14-2 7-benzyloxy-2-octene-1,4-diol 
• 370863-13-1 7-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)oxy-2-octene-4-ol 
• 96556-29-5 3-(benzyloxy)-1-butyl p-toluenesulfonate 
• 1485-70-7 N-benzylbenzamide 
• 10264-14-9 N-benzylbutyramide 

Relevant academic research and scientific papers

Macro-cyclic immuno-modulator

The invention provides a macro-cyclic immuno-modulator, and discloses a compound shown as a formula I, and a tautomer, an enantiomer, a pharmaceutically acceptable salt, a crystal form, hydrate or solvate thereof. Experiment results show that the compound can be effectively combined with STING and has a good STING protein excitation function. Therefore, the compound can be used as an STING agonist, can be used to treat various related diseases, and has a very good application prospect in preparing medicines for treating diseases related to STING activity, especially medicines for treating inflammatory and autoimmune diseases, infectious diseases, cancers or precancerous syndromes.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

Intramolecular OH...Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif

Fluorination is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen-bond (HB) properties of adjacent functional groups, as well as the HB-accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH...F intramolecular HBs (IMHBs) has been established for conformationally restricted fluorohydrins, such interaction in flexible compounds remained questionable. Herein is demonstrated for the first time - and in contrast to earlier reports - the occurrence of OH...F IMHBs in acyclic saturated γ-fluorohydrins, even for the parent 3-fluoropropan-1-ol. The relative stereochemistry is shown to have a crucial influence on the corresponding h1JOH...F values, as illustrated by syn- and anti-4-fluoropentan-2-ol (6.6 and 1.9 Hz). The magnitude of OH...F IMHBs and their strong dependence on the overall molecular conformational profile, fluorination motif, and alkyl substitution level, is rationalized by quantum chemical calculations. For a given alkyl chain, the "rule of shielding" applies to OH...F IMHB energies. Surprisingly, the predicted OH...F IMHB energies are only moderately weaker than these of the corresponding OH...OMe. These results provide new insights of the impact of fluorination of aliphatic alcohols, with attractive perspectives for rational drug design.

Metal trifluoromethanesulfonate-catalyzed regioselective reductive ring opening of benzylidene acetals

A systematic study of various metal trifluoromethanesulfonates as efficient catalysts in the regioselective reductive ring opening of benzylidene acetals is described, including the effects of solvents, reducing agents, and temperature. These catalysts are found to be effective in cleaving the 4,6-O-acetal rings of hexopyranosides at either O4 or O6, respectively. When used in conjunction with a 1 M solution of BH3.THF in THF without extra addition of any solvent, it affects the ring fission at the O6 position to generate the corresponding primary alcohols, whereas O4-opening takes place in acetonitrile in the presence of dimethylethylsilane as the reductant leading to the secondary hydroxyl derivatives in high selectivity and yields. These methodologies can be applied to a wide range of substrates containing various functional groups.

Total synthesis of the proposed structure of the anthrapyran metabolite δ-indomycinone

The first total synthesis of the proposed structure of δ-indomycinone has been accomplished. The key steps involve the Diels-Alder reaction of a bromonaphthoquinone (6) and 1-methoxy-3-methyl-1-trimethylsiloxy-1,3-butadiene (7) to access the anthraquinone

Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals

(Chemical Equation Presented) Reducing the choices. Cu(OTf)2 is an efficient and dual-purpose catalyst for the highly regioselective reductive ring openings of benzylidene acetals with either BH3 or Me 2EtSiH to give the corresponding primary and secondary alcohols (see scheme). Isotope studies have confirmed that both modes of ring cleavage proceed by an SN1 reaction pathway when borane or silane attack the acetal carbon center.

Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: Application in the formal synthesis of macrosphelide A

An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transfor

Reactions of trialkylalanes with cyclic acetals and orthoformates in CH2Cl2 and ClCH2CH2Cl as solvents

Under mild conditions, trialkylalanes (Et3Al and Bu i3Al) in chlorine-containing solvents (CH 2Cl2 or ClCH2CH2Cl) react with cyclic acetals and orthoformates to form glycol monoethers and dialkylacetals, respectively, in high yields. The 1H NMR spectroscopic data demonstrate that CH2Cl2 or ClCH2CH 2Cl interacts with Bui3Al.

An efficient synthesis of trans-γ-oxo-α,β-unsaturated carboxylic acids, the intermediates for patulolide A and pyrenophorin

An efficient synthesis of intermediates for macrolide antifungals patulolide A 14 and pyrenophorin 16 are described with the key steps involving (i) coupling of the alkyl lithium with α,β-unsaturated aldehyde 8, (ii) the oxidation of the cis-trans mixture

REGIOSPECIFIC CLEAVAGE OF 1,3-DIOXANES BY ORGANOALUMINUM COMPOUNDS

Organoaluminum compounds react with 4-methyl-2-phenyl-1,3-dioxane with cleavage of the O1-C2 bond to give monoethers with a primary alcohol group.