106356-53-0

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Ipc2B(allyl), 1M in dioxane is used as a chiral allyl borane reagent for the asymmetric allylation of aldehydes. This process is crucial in the synthesis of chiral homoallylic alcohols, which serve as key intermediates in the development of various pharmaceutical compounds. The use of this reagent allows for the creation of enantiomerically pure products, which is essential for the efficacy and safety of many drugs.
Used in Chemical Industry:
In the chemical industry, (+)-Ipc2B(allyl), 1M in dioxane is employed as a versatile reagent for the synthesis of chiral homoallylic alcohols. These chiral compounds are valuable building blocks in the production of various specialty chemicals, including agrochemicals, fragrances, and other fine chemicals. The use of this reagent enables the efficient and selective synthesis of these chiral compounds, contributing to the overall productivity and sustainability of the chemical industry.
General Description:

Upstream product

• 99438-28-5 (+)-B-methoxydiisocamphenylborane 
• 1730-25-2 allylmagnesium bromide 
• 112246-73-8 B-chlorodiisopinocampheylborane 
• 2622-05-1 allylmagnesium bromide 
• 1826-67-1 vinyl magnesium bromide 
• 85116-37-6 (-)-diisopinocamphenylborane chloride 
• 21947-87-5 L-diisopinocampheylborane 
• 7785-26-4 (-)-α-pinene 

Downstream Products

• 99328-46-8 (4R,5S)-5-Methyl-hept-1-en-4-ol 
• 99342-24-2 (4S,5S)-5-Methyl-hept-1-en-4-ol 
• 89046-67-3 (2S,3R)-2-methyl-1-(phenylmethoxy)hex-5-en-3-ol 
• 106357-32-8 (2S,3S)-1-(benzyloxy)-2-methylhept-5-en-3-ol 
• 186417-90-3 (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one 
• 144635-03-0 (S)-1-(pyridin-3-yl)but-3-en-1-ol 
• 314280-28-9 (R)-1-(pyridin-3-yl)but-3-en-1-ol 
• 350592-77-7 (S,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene 
• 350592-79-9 (R,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene 
• 343262-83-9 (E)-(4S,5R,6S)-6-(tert-butyldiphenylsilanoxy)-5-methylnon-1,7-diene-4-ol 
• 132313-09-8 (1R)-1-(4-bromophenyl)-3-butenylamine 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 
• 488703-70-4 (4R,5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of the C1-C12 fragment of the cytotoxic macrolide FD-891

A stereoselective synthesis of the C1-C12 fragment of the naturally occurring, cytotoxic macrolide FD-891, is described. The initial chirality was created via an asymmetric Evans aldol reaction. Two other asymmetric reactions, a Sharpless epoxidation and

Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules

The preparation of a series of pironetin analogues with simplified structure is described. Their cytotoxic activity and their interactions with tubulin have been investigated. It has been found that, while less active than the parent molecule, the pironetin analogues still share the mechanism of action of the latter and compete for the same binding site to α-tubulin. Variations in the configurations of their stereocenters do not translate into relevant differences between biological activities.

Stereoselective synthesis of (-)-galantinic acid

An efficient and highly concise synthesis of (-)-galantinic acid has been achieved using an asymmetric allylation reaction of Garner's aldehyde. Georg Thieme Verlag Stuttgart - New York.

Total syntheses of (-)-macrolactin a, (+)-macrolactin e, and (-)- macrolactinic acid: An exercise in stille cross-coupling chemistry

The total syntheses of the potent antiviral agent (-)-macrolactin A (1) and two related family members, (+)-macrolactin E (5) and (-)-macrolactinic acid (7), have been achieved, exploiting a unified, convergent, and highly stereocontrolled strategy. Extensive use of the palladium-catalyzed Stille cross-coupling reaction for the stereospecific construction of the three isolated dienes including macrocyclization formed the cornerstone of the successful strategy. The total syntheses of these natural products, no longer available via fermentation, confirm their relative and absolute stereochemistries and provide access to possible analogues for further biological study.

Total Synthesis and Tentative Structural Elucidation of Cryptomoscatone E3: Interplay of Experimental and Computational Studies

A successful combination of computational chemistry and total synthesis was explored to tentatively elucidate the absolute configuration of cryptomoscatone E3, a polyketide isolated from the Brazilian tree Cryptocarya mandiocanna. Two independent synthetic approaches are discussed based on asymmetric allylation, ring closing metathesis, and aldol reactions.

Studies toward the Total Synthesis of Caribbean Ciguatoxin C-CTX-1: Synthesis of the LMN-Ring Fragment through Reductive Olefin Cross-Coupling

Synthesis of the LMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the principal causative toxin for ciguatera fish poisoning around the Caribbean Sea areas, is described. The key feature of the synthesis is the stereoselective introduction of an angular methyl group on the sterically encumbered seven-membered M-ring by the application of a hydrogen atom transfer-based reductive olefin coupling.

Enantioselective Total Synthesis of Diocollettines A

The first enantioselective total synthesis of diocollettines A was accomplished in only six steps from a known compound. A short and practical synthetic route was disclosed, featuring an intensive investigation of the stereoselective aldol reaction as a key step using an easily prepared aldehyde moiety and an enone derivative. The synthetic scheme also includes the efficient stereocontrolled construction of the tricyclic skeleton of diocollettines A by intramolecular acetal formation, stereoselective dihydroxylation, and intramolecular ether cyclization.

Total synthesis and configurational assignment of the marine natural product haliclamide

The marine natural product haliclamide has been synthesized based on macrocyclization by ring-closing olefin metathesis. Using either enantiomer of two of the four building blocks that were employed to assemble the diene precursor for the metathesis reaction, three non-natural isomers of haliclamide were also prepared. On the basis of the comparison of the 1H and 13C NMR spectra of the individual stereoisomers with literature data for the natural product, the configuration of the previously unassigned stereocenters at C9 and C20 of haliclamide could be determined to be S for both carbons. The absolute configuration of haliclamide thus is 2S, 9S, 14R, 20S. The antiproliferative activity of synthetic haliclamide against several human cancer cell lines was found to be in the high μM range. The compound showed no antifungal or antibiotic activity.

Studies on C18-C20 aldol couplings of rhizopodin

The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection. Georg Thieme Verlag Stuttgart. New York.

Synthesis and pharmacological properties of 5-alkyl substituted nicotine analogs

This paper describes a concise and practical route to enantiomerically enriched 5-alkyl substituted nicotine analogs. The Vilsmeier reaction was used to construct the nicotinaldehydes ring followed by the introduction of the chiral homoallylic alcohol by organic boron reagent and the cyclization of the pyrrolidine ring through the reduction of a chiral azide. 17 analogs have been synthesized and their corresponding biological activities were tested, in which compounds 10d and 10g exhibit excellent IC50 values against RD and SY-SY5Y. Copyright