25791-20-2

Usage

Uses

Used in Organic Synthesis:
(1-TETRADECYL)TRIPHENYLPHOSPHONIUM BROMIDE is used as a key intermediate for the synthesis of various organic compounds. Its ability to form stable complexes with other molecules makes it a valuable component in the creation of new chemical entities.
Used in Pharmaceuticals:
In the pharmaceutical industry, (1-TETRADECYL)TRIPHENYLPHOSPHONIUM BROMIDE serves as an essential raw material for the development of new drugs. Its unique chemical structure allows it to interact with biological targets, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemicals:
(1-TETRADECYL)TRIPHENYLPHOSPHONIUM BROMIDE is utilized as a vital component in the formulation of agrochemicals, such as pesticides and herbicides. Its effectiveness in controlling pests and promoting crop growth makes it a valuable asset in the agricultural sector.
Used in Dyestuff:
In the dyestuff industry, (1-TETRADECYL)TRIPHENYLPHOSPHONIUM BROMIDE is employed as a crucial intermediate for the production of various dyes and pigments. Its ability to impart color and stability to textiles and other materials contributes to its significance in this field.

InChI:InChI=1/C32H44P.BrH/c1-2-3-4-5-6-7-8-9-10-11-12-22-29-33(30-23-16-13-17-24-30,31-25-18-14-19-26-31)32-27-20-15-21-28-32;/h13-21,23-28H,2-12,22,29H2,1H3;1H/q+1;/p-1

Upstream product

• 112-71-0 1-Bromotetradecane 
• 603-35-0 triphenylphosphine 
• 629-72-1 pentadecyl bromide 

Downstream Products

• 27519-02-4 (Z)-tricos-9-ene 
• 163212-18-8 Benzoic acid (4S,5S)-2,2-dimethyl-5-((Z)-pentadec-1-enyl)-[1,3]dioxolan-4-ylmethyl ester 
• 143516-95-4 N-{(E)-(1S,2R)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-acetamide 
• 143516-95-4 N-{(E)-(1R,2S)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-acetamide 
• 102874-34-0 [(4S,5R)-5-((E)-Pentadec-1-enyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-methanol 
• 147910-01-8 (2S,3R,4Z)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene 
• 147910-00-7 (2S,3R,4E)-3-(benzyloxymethoxy)-1-(tert-butyldimethylsiloxy)-2-(octadecanoylamino)-4-octadecene 
• 123447-03-0 <2(S),3(R),4Z>-2-amino-1-O-(tert-butyldiphenylsilyl)-2-N,3-O-carbonyl-4-ocatadecene-1,3-diol 
• 123447-09-6 <2(S),3(R),4E>-2-amino-1-O-(tert-butyldiphenylsilyl)-2-N,3-O-carbonyl-4-octadecene-1,3-diol 
• 152386-86-2 (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol 
• 96854-01-2 triphenylphosphoniotetradecylid 
• 132697-84-8 (2R,3S)-1,3-O-benzylidene-4-octadecene-1,2,3-triol 
• 117112-62-6 (2R,3R)-cis-1,3-O-benzylidene-1,2,3-octadec-4-enetriol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 

Relevant academic research and scientific papers

Α - galactose ceramide new isomer and its synthetic method

The invention provides an alpha-galactosyl ceramide new isomer and its synthetic method. Configuration of sphingosine chain is changed to 4,5-cis double bond sphingosine chain. According to the invention, reaction steps are shortened, yield is raised, and aftertreatment and purification steps are omitted. The synthetic method can be used for total synthesis of similar glycosyl ceramide and satisfies wide range of development, research and application of different glycosyl ceramide.

The convergent total synthesis of cytotoxic homospisulosine and its 3-epi-analogue

A common strategy for the total synthesis of cytotoxic homospisulosine 7 and its 3-epi-analogue 10 was achieved in a stereoconvergent manner, from 3,5-di-O-benzyl-d-xylofuranose with the efficient use of rearranged products 14-17. The key transformations of this approach are [3,3]-heterosigmatropic rearrangements of allylic substrates 18 and 19 to establish a stereogenic amino group and regioselective intramolecular cyclization to form common oxazolidinones 28 and 29. Elongation of the side chain was accomplished via a Wittig reaction. Several compounds were evaluated for their in vitro antiproliferative/cytotoxic activity by the MTT method employing five different human cancer cell lines (Jurkat, MDA-MB-231, MCF-7, HCT-116 and Caco-2). The obtained data revealed that homospisulosine 7 exhibited the most significant inhibitory effects among all of the screened compounds on the panel of the tested cell lines with IC50 values comparable to those of conventional anticancer agents such as cisplatin and etoposide.

Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols

We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.

Stereoselective synthesis of N,O,O,O-tetraacetyl-D-ribo-phytosphingosine, N,O,O-triacetyl-D-erythro-sphingosine and N,O,O-triacetyl sphingonine from a common chiral intermediate derived from D-mannitol

An efficient protocol for the stereoselective synthesis of tetraacetyl-D-ribo-hytosphingosine, triacetyl-D-erythro-sphingosine and triacetyl sphinganine has been devised from a common chiral intermediate derived from commercially available D-mannitol. The key steps involved are Sharpless epoxidation, Miyashita C(2) selective endo mode azide opening of 2,3-epoxy alcohol, and selective E-Wittig olefination. ARKAT-USA, Inc.

α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives

Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

GLYCOLIPIDS AND ANALOGUES THEREOF AS ANTIGENS FOR NK T CELLS

This invention relates to immunogenic compounds which may serve as ligands for NKT (natural killer T) cells and to methods of use thereof in modulating immune responses.

The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.

Close-range attraction in Lygocoris pabulinus (L.)

Males of the green capsid bug, Lygocoris pabulinus, exhibit a specific courtship behavior, i.e., a vibration of the abdomen. When both live and dead females were offered to males, this vibration behavior was elicited in most of the males tested. When females were dissected into separate body parts, heads, wings, and legs elicited equal responses, while thorax plus abdomen elicited a much lower response. When separate body parts were extracted, the leg extracts elicited significantly stronger responses than any other extract. This suggests that female L. pabulinus legs are either the source of a close-range sex pheromone or that pheromone is accumulated on the legs due to grooming behavior. The leg extracts contained several hydrocarbons such as n-alkenes, n-alkanes, and some methylalkanes. Female extracts contained more (Z)-9-pentacosene and male extracts contained more (Z)-9-heptacosene. Substrates on which females had walked elicited similar responses as female legs, indicating that the pheromone is deposited on the substrate. This enlarges the functional range of low-volatility compounds, which are thought to function only when sexes are in close vicinity or in contact.

Synthesis and biological activity of new diarylalkenes

Condensation of 5-nitro-, 3-chloro-, and 5-chlorosalicylic acid with formaldehyde afforded dimeric disalicylmethanes which were O-methylated with dimethyl sulfate and oxidized with chromium(VI) oxide to give the diarylketones 10, 11, 12. Wittig reaction with ylides obtained by deprotonation of alkyltriphenylphosphonium salts with sodium bis (trimethylsilyl)amide yielded a series of diarylalkenes. Some of the obtained compounds showed high antimicrobial activity in vitro against Bacillus subtilis and Mycobacterium smegmatis.