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Piers-Rubinsztajn reaction to unlock an 8-step synthesis of 7-hydroxy cannabidiol.

ABSTRACT: A scalable synthesis of 7-hydroxy cannabidiol (7-OH CBD), a primary metabolite of (-)-cannabidiol (CBD), is highly desirable, from an industrial point of view, to enable future clinical trials. A Piers-Rubinsztajn reaction was key to enable a mild deprotection and a concise synthesis of 7-OH CBD from commercially available CBD, in 31% overall yield.

SUBMITTER: Cocco E

PROVIDER: S-EPMC10790624 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Piers-Rubinsztajn reaction to unlock an 8-step synthesis of 7-hydroxy cannabidiol.

Cocco Emanuele E Iapadre Debora D Brusa Alessandro A Allegrini Pietro P Thomas Stephen P SP Pesciaioli Fabio F Carlone Armando A

RSC advances 20240116 4

A scalable synthesis of 7-hydroxy cannabidiol (7-OH CBD), a primary metabolite of (-)-cannabidiol (CBD), is highly desirable, from an industrial point of view, to enable future clinical trials. A Piers-Rubinsztajn reaction was key to enable a mild deprotection and a concise synthesis of 7-OH CBD from commercially available CBD, in 31% overall yield. ...[more]

PMID: 38229717

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Hyperbranched Polycarbosiloxanes: Synthesis by Piers-Rubinsztajn Reaction and Application as Precursors to Magnetoceramics.

Project description:Silicon-containing hyperbranched polymers (Si-HBPs) have drawn much attention due to their promising applications. However, the construction of Si-HBPs, especially those containing functional aromatic units in the branched backbones by the simple and efficient Piers-Rubinsztajn (P-R) reaction, has been rarely developed. Herein, a series of novel hyperbranched polycarbosiloxanes were prepared by the P-R reactions of methyl-, or phenyl-triethoxylsilane and three Si-H containing aromatic monomers, including 1,4-bis(dimethylsilyl)benzene, 4,4'-bis(dimethylsilyl)-1,1'-biphenyl and 1,1'-bis(dimethylsilyl)ferrocene, using B(C6F5)3 as the catalyst for 0.5 h at room temperature. Their structures were fully characterized by Fourier transform infrared spectroscopy, 1H NMR, 13C NMR, and 29Si NMR. The molecular weights were determined by gel permeation chromatography. The degrees of branching of these polymers were 0.69-0.89, which were calculated based on the quantitative 29Si NMR spectroscopy. For applications, the ferrocene-linked Si-HBP can be used as precursors to produce functional ceramics with good magnetizability after pyrolysis at elevated temperature.

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Scalable Synthetic Route to PDMS Ring Polymers in High Yields from Commercially Available Materials Using the Piers-Rubinsztajn Reaction

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Use of Piers-Rubinsztajn Chemistry to Access Unique and Challenging Silicon Phthalocyanines.

Project description:Axial functionalization is one mode that enables the solubility of silicon phthalocyanines (SiPcs). Our group observed that the use of typical axial functionalization methodologies on reaction of Cl2SiPc with the chlorotriphenyl silane reagent unexpectedly resulted in the equal formation of triphenyl silyloxy silicon tetrabenzotriazacorrole ((3PS)-SiTbc) and the desired bis(tri-phenyl siloxy)-silicon phthalocyanine ((3PS)2-SiPc). The formation of a (3PS)-SiTbc was unexpected, and the separation of (3PS)-SiTbc and (3PS)2-SiPc was difficult. Therefore, in this study, we investigated the use of Piers-Rubinsztajn (PR) chemistry as an alternative method to functionalize the axial position of a SiPc to avoid the generation of a Tbc derivative. PR chemistry is a novel method to form a Si-O bond starting with a Si-H-based reactant and a -OH-based nucleophile enabled by tris(pentafluorophenyl)borane as a catalyst. The PR chemistry was screened on several fronts on how it can be applied to SiPcs. It was found that the process needs to be run in nitrobenzene at a molar ratio and at a particular temperature. To this end, the triphenylsiloxy derivative (3PS)2-SiPc was produced and fully characterized, without the production of a Tbc derivative. In addition, we explored and outlined that the PR chemistry method can enable the formation of other SiPc derivatives that are inaccessible utilizing other established axial substitution chemistry methods such as (TM3)2-SiPc and (MDM)2-SiPc. These additional materials were also physically characterized. The main conclusion is that the PR chemistry method can be applied to SiPcs and yield several alternative derivatives and has the potential to apply to additional macrocyclic compounds for unique derivative formation.

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Fabrication of Reactive Poly(Phenyl-Substituted Siloxanes/Silsesquioxanes) with Si‒H and Alkoxy Functional Groups via the Piers⁻Rubinsztajn Reaction.

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Tandem metabolic reaction-based sensors unlock in vivo metabolomics.

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Pyrophosphate hydrolysis is an intrinsic and critical step of the DNA synthesis reaction.

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