28322-40-9

Usage

Uses

Used in Pharmaceutical Industry:
ISOAMYLTRIPHENYLPHOSPHONIUM BROMIDE is used as a reactant for the preparation of 9,11-secosterol analogs, which are potential antitumor agents. These analogs have shown promise in the development of new cancer treatments.
Used in Chemical Synthesis:
ISOAMYLTRIPHENYLPHOSPHONIUM BROMIDE is used as a reactant in the synthesis of antiepileptic compounds, such as ceramide I and its triacetyl derivatives. This is achieved through olefin cross metathesis, a widely used method in organic chemistry for the formation of carbon-carbon double bonds.
Used in Organic Chemistry:
In the field of organic chemistry, ISOAMYLTRIPHENYLPHOSPHONIUM BROMIDE is used as a reactant for the preparation of meso-epoxides. This is done through a series of reactions involving the substitution of alkyl bromides with triphenylphosphine, followed by Wittig olefination and epoxidation. Meso-epoxides are important intermediates in the synthesis of various biologically active compounds and pharmaceuticals.
Overall, ISOAMYLTRIPHENYLPHOSPHONIUM BROMIDE is a valuable compound in the fields of pharmaceuticals, chemical synthesis, and organic chemistry, playing a crucial role in the development of new drugs and the synthesis of various organic compounds.

InChI:InChI=1/C23H26P.BrH/c1-20(2)18-19-24(21-12-6-3-7-13-21,22-14-8-4-9-15-22)23-16-10-5-11-17-23;/h3-17,20H,18-19H2,1-2H3;1H/q+1;/p-1

Upstream product

• 603-35-0 triphenylphosphine 
• 107-82-4 i-pentyl bromide 

Downstream Products

• 46941-66-6 (3-methylbutan-1-yl)(diphenyl)phosphine oxide 
• 39110-24-2 (3-Methyl-butylidene)-triphenyl-λ⁵-phosphane 
• 201654-82-2 2-(isohex-1'-enyl)benzoic acid 
• 168984-14-3 4-((1E,3E)-2,6-Dimethyl-hepta-1,3-dienyl)-benzoic acid ethyl ester 
• 93495-41-1 p-(2,6,10-trimethylundecyl)benzoic acid 
• 65032-30-6 1-cyclohexylidene-3-methylbutane 
• 93495-42-2 p-(2,6-dimethylheptyl)benzoic acid 
• 168984-15-4 4-((1E,3E)-2,6-Dimethyl-hepta-1,3-dienyl)-benzoic acid 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 119618-56-3 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene 
• 1374645-89-2 (1R,4S,E)-1-isopropyl-4-methyl-2-(3-methylbutylidene)cyclohexane 
• 212838-91-0 ((E)-13-Methyl-tetradec-10-enyloxymethyl)-benzene 
• 104882-08-8 cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene 
• 104882-09-9 trans-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene 

Relevant academic research and scientific papers

Method for removing triphenylphosphine oxide

The invention discloses a method for removing triphenylphosphine oxide. The method comprises: adding water into a reaction mixture of the compound shown in the formula I and isopentyltriphenylphosphine bromide for quenching reaction, adding an extracting agent into the reaction mixture, stirring, standing for layering, and washing an obtained organic phase with water; concentrating under reduced pressure, replacing with methanol to be thick, cooling to crystallize, filtering, and drying a filter cake to obtain a compound shown as a formula II which basically does not contain triphenylphosphine; or carrying out water precipitation to obtain the compound shown in the formula II which basically does not contain triphenylphosphine oxide.

SYNTHETIC INNATE IMMUNE RECEPTOR LIGANDS AND USES THEREOF

An adjuvant formulation includes a monophosphoryl Lipid A (MPLA) analogue, a Pam3CSK4 analogue, or a muramyldipeptide (MDP) analogue, or combinations thereof. The adjuvant may be formulated in soluble form or in a nanoparticle, such as polylactic glycolic acid nanoparticles. A vaccine formulation comprises the adjuvant formulation and an immunogen. Methods of vaccinating an animal include delivering the vaccine formulation to the animal.

Screening of a virtual mirror-image library of natural products

We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using d-protein technology. In this process, two chemical syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds.

Scandium-bipyridine-catalyzed enantioselective aminolysis of meso-epoxides

The scandium-bipyridine-catalyzed enantioselective addition of anilines and O-alkyl hydroxylamines to meso-epoxides has been optimized and extended to a broad range of epoxides and amines. Whereas aromatic meso-epoxides generally furnished the corresponding 1.2-amino alcohols in Excellent enantioselectivities, aliphatic meso-epoxides only gave rise to moderate enantioselectivities in the aminolysis. The catalyst loading may be lowered to just 5 mol% with only marginal effects on yield and enantioselectivity. A strong positive nonlinear effect has been observed, pointing to aggregation phenomena of the catalyst.

Conjugated dienes as prohaptens in contact allergy: In vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation

There is a great interest in developing in vitro/in silico methods for the prediction of contact allergenic activity. However, many proposed methods do not take the activation of prohaptens to sensitizers by skin metabolism into account. As a consequence, consumer products containing potent sensitizers could be marketed. To identify prohaptens, studies regarding their structure-activity relationships and the mechanisms of their activation must be conducted. In the present investigation, we have studied the structure-activity relationships for alkene prohaptens. A series of seven alkenes (1-7), all of the same basic structure but with variation in the number and position(s) of the double bond(s), were designed and screened for sensitizing capacity using the murine local lymph node assay. Compounds 1-7 were also incubated with liver microsomes in the presence of glutathione to trap and identify reactive metabolites. The metabolic conversion of three alkenes (9-11) to epoxides (12-15) was also studied along with comparison of their sensitizing capacity. Our results show that conjugated dienes in or in conjunction with a six-membered ring are prohaptens that can be metabolically activated to epoxides and conjugated with GSH. Related alkenes containing isolated double bonds and an acyclic conjugated diene were shown to be weak or nonsensitizers. For the first time, the naturally occurring monoterpenes α-phellandrene, β-phellandrene, and α-terpinene were demonstrated to be prohaptens able to induce contact allergy. The difference in sensitizing capacity of conjugated dienes as compared to alkenes with isolated double bonds was found to be due to the high reactivity and sensitizing capacity of the allylic epoxides metabolically formed from conjugated dienes. We recommend that these structure-activity relationship rules are incorporated into in silico predictive databases and propose that the prediction of contact allergenic activity of suspected prohaptens is based on assessment of susceptibility to metabolic activation and chemical reactivity of potential metabolites.

SUBSTITUTED ARYLCYCLOPROPYLACETAMIDES AS GLUCOKINASE ACTIVATORS

According to the present invention there is provided a compounds of formula (I): and pharmaceutically acceptable salts thereof.

An efficient synthesis of sulfobacin A (flavocristamide B), sulfobacin B, and flavocristamide A

Sulfobacin A (flavocristamide B, 1), sulfobacin B (2), and flavocristamide A (3), biologically active sulfonolipids, have been efficiently synthesized utilizing the asymmetric aldol reaction of the Schiff base 8 derived from glycine ester and (+)-2-hydroxy-3-pinanone (HyPN). (C) 2000 Elsevier Science Ltd.

Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin

Topostins B567 (2b) and D654 (3b) (WB-3559D, flavolipin) have been efficiently synthesized from 1,10-decanediol (5)in 11 and 13 steps, respectively, involving an asymmetric hydrogenation of the β-keto ester 14 using (R)-BINAp ruthenium bromide and a peptide coupling using diethyl phosphorocyanidate (DEPC, (EtO)2P(O)CN) as key steps.

Total synthesis of sulfobacin A (flavocristamide B)

Sulfobacin A (1), a novel von Willebrand factor receptor antagonist isolated from the culture broth of Chryseobacterium sp. NR 2993, was efficiently synthesized for the first time.

Synthesis of [1.1.1]propellanes by bridging of bicyclo[1.1.0]butanes

Several [1.1.1]propellanes were synthesized by bridging the 1,3-positions of the corresponding bicyclo[1.1.0]butane. The synthesis of 1-bromo-3-(chloromethyl)bicyclobutanes and the bridging were carried out in a one-pot reaction by addition of 2.0 equiv. of MeLito 1,1-dibromo-2,2-bis(chlormethyl)-cyclopropanes 10. Three routes to 10 were investigated: Firstly, the Wittig reaction of 1,3-dichloroacetone leading to (chloromethyl)allyl chlorides 6 was, with the exception of 6m, successful only with Wittig reagents derived from primary alkyl halides. Secondly, reduction of diethyl alkylidenemalonates with LiAlH4 in benzene afforded carbinols 12 which were converted into 6 by reaction with N-chlorosuccinimide/ dimethyl sulfide. The cyclopropanation of 6 to 10 was achieved by reaction with bromoform/NaOH under phase-transfer catalysis conditions. Finally, starting from diethyl alkylidenemalonates, the sequence of reduction and cyclopropanation could be interchanged, according to the sequence 11 → 13 → 14 → 10. Propellanes 5b and 3 were reduced with LiAlH4 to bicyclo[1.1.1]pentanes 15b and e. 2-D INADEQUATE NMR spectra of 5d and 5p indicate that the coupling constants J(13C-13C) between the bridgehead positions are very small, i.e. 0.47 and 0.53 Hz, respectively. VCH Verlagsgesellschaft mbH, 1996.